{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-65b545b2ce404f6ab07d9ff218ea13d7","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"de376779bac1f3c56aabebef0ee7f31a3ca896d4345038265c7c762d91daf16e","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-65b545b2ce404f6ab07d9ff218ea13d7-f960a139e5f9","ord-65b545b2ce404f6ab07d9ff218ea13d7-6f5035e02686"],"reactant_slugs":["ord-compound-7d2acc558623051e5c91","ord-compound-c548c24d29328ab9f616"],"product_slugs":["ord-compound-623ee6ba5f18f4479b7f"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lsf_lit_minisci_113"},{"type":"CUSTOM","details":"rxn_tech from SURF table","value":"alkylation"},{"type":"REACTION_TYPE","details":"alkylation minisci","value":"alkylation minisci"}],"inputs":{"additive_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)(O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7664-93-9"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)N1CC(I)C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"254454-54-1"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OC(C=1C=CN=C2C=CC(OC)=CC21)C3N4CCC(C3)C(C4)CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"522-66-7"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Fe].O=S(=O)(O)O.O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7782-63-0"}],"amount":{"moles":{"value":0.6,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OO"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7722-84-1"}],"amount":{"moles":{"value":6,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7732-18-5"}],"amount":{"volume":{"value":0.6,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-68-5"}],"amount":{"volume":{"value":9.4,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"notes":{"procedure_details":"H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise  over  1-2  min  to  a  stirred  solution  of  6-methoxy-4-methylquinoline  4a  (173  mg,  1.0  mmol),  concentrated  H2SO4  (107  μL,  2.0  mmol),  3-iodooxetane  (368  mg,  2.0  mmol)  and  iron(II)  sulfate  heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of  iron(II)  sulfate  heptahydrate  (80  mg,  0.3  mmol)  was  added  and  the  mixture  was  stirred  at  room  temperature for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 15 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were dried (MgSO4), filtered and the  - 16 -solvent  removed  under  vacuum  to  leave  a  crude  oil.  The  oil  was  purified  by  preparative  thin-layer  chromatography using 30% EtOAc / hexanes as eluent to give recovered 6-methoxy-4-methylquinoline 4a (32 mg, 19%), a mixture of 6-methoxy-4-methylquinoline 4a and the desired product 5a (15 mg) and the  desired  product  5a  (72  mg,  31%)  as  a  solid.  An  analytical  portion  of  the  product  5a  was  recrystallized from hexanes for data purposes"},"outcomes":[{"reaction_time":{"value":0.75,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)N1CC(C2=NC=3C=CC(OC)=CC3C(=C2)C(O)C4N5CCC(C4)C(C5)CC)C1"},{"type":"CAS_NUMBER","value":"1180653-98-8"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":17}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ 7.96 (d, J = 9.2 Hz, 1H), 7.38-7.35  (m,  2H),  7.19  (d, J  =  2.6  Hz,  1H),  5.15  (dd,  J =  8.3,  5.9  Hz,  2H),  5.03  (t, J  =  6.2  Hz,  2H),  4.52-4.44 (m, 1H), 3.96 (s, 3H), 2.68 (s, 3H); 13C NMR (100 MHz; CDCl3) 158.1, 157.6, 143.9, 143.6, 131.2, 128.1, 121.6, 120.3, 102.1, 77.1, 55.7, 42.5, 19.2."}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-7d2acc558623051e5c91","name":"C20H26N2O2 · ORD LJOQGZACKSYWCH-UHFFFAOYSA-N","smiles":"CCC1CN2CCC1CC2C(O)c1ccnc2ccc(OC)cc12","inchi":"InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3","formula":"C20H26N2O2"},{"slug":"ord-compound-c548c24d29328ab9f616","name":"C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)N1CC(I)C1","inchi":"InChI=1S/C8H14INO2/c1-8(2,3)12-7(11)10-4-6(9)5-10/h6H,4-5H2,1-3H3","formula":"C8H14INO2"},{"slug":"ord-compound-623ee6ba5f18f4479b7f","name":"C28H39N3O4 · ORD RBYUYDNLIGPELY-UHFFFAOYSA-N","smiles":"CCC1CN2CCC1CC2C(O)c1cc(C2CN(C(=O)OC(C)(C)C)C2)nc2ccc(OC)cc12","inchi":"InChI=1S/C28H39N3O4/c1-6-17-14-30-10-9-18(17)11-25(30)26(32)22-13-24(29-23-8-7-20(34-5)12-21(22)23)19-15-31(16-19)27(33)35-28(2,3)4/h7-8,12-13,17-19,25-26,32H,6,9-11,14-16H2,1-5H3","formula":"C28H39N3O4"}],"dataset":{"dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","name":"Minisci dataset from Roche","description":"Minisci reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":130,"path":"data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","sha256":"ebefbe9aba687f182d4f068e94be0f7fd71d1189bdb2eff2aca6fedf4d522bf3","bytes":37643,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet"},"publication":{"slug":"ord-publication-91c8bf15879e5ce2","title":"Literature experiment — 10.1021/jo9010624","source_type":"paper","doi":"10.1021/jo9010624","url":"https://doi.org/10.1021/jo9010624","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}