{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-6c6bc5ae0eb34da6b5c49cf73fe096b5","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"f3a19f3c056bb0d9de4cc7ef03d1b5d63b66f720b9d01b11b0da45fba501aeab","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-6c6bc5ae0eb34da6b5c49cf73fe096b5-ceca4a63b78e","ord-6c6bc5ae0eb34da6b5c49cf73fe096b5-622650e8fb86"],"reactant_slugs":["ord-compound-b4ed7a20eab53f680d31","ord-compound-7a5ea1f0381bb40c0ab8"],"product_slugs":["ord-compound-55705f10a0dd8d75bdea"],"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_118"},{"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":"IC1COC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"26272-85-5"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N1=CC2=CC=CC=C2C=C1C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1125-80-0"}],"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":40,"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  3  min  to  a  stirred  solution  of  3-methylisoquinoline  1c  (143  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 40 °C. After 3 min a further portion of iron(II) sulfate heptahydrate (80 mg,  - 5 -(80 mg, 0.3 mmol) was added and the mixture was stirred at 40 °C for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added over 2 min, and the mixture was stirred at 40 °C for 20 min, then poured into 0.2 M solution of NaOH (20 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 washed with brine (25 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil (364 mg). The oil was dry-loaded on to silica (750 mg) and purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 3:7) to give the desired  product  2c  (99  mg,  ca.  93%  purity,  46%  yield  adjusted  for  purity)  as  a  solid.  The  solid  was  purified  further  by  column  chromatography  on  silica  gel  using  EtOAc  /  hexanes  (0:1  to  1:4  slow  gradient   then   to   3:7)   as   eluent   (to   give   67   mg,   96%   purity),   then   by   recrystallization   from   methylcyclohexane  to  give  material  for  data  purposes. "},"outcomes":[{"reaction_time":{"value":0.8,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C(=CC=2C=CC=CC2C1C3COC3)C"},{"type":"CAS_NUMBER","value":"1180653-58-0"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":46}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H  NMR  (400  MHz;  CDCl3) δ  7.76  (d,  J  =  8.2  Hz, 1H), 7.67-7.60 (m, 2H), 7.48 (t, J = 7.5 Hz, 1H), 7.39 (s, 1H), 5.29-5.26 (m, 2H), 5.21-5.17 (m, 2H), 5.08-5.00  (m,  1H),  2.70  (s,  3H);  13C  NMR  (100  MHz;  CDCl3) δ  158.7,  150.7,  137.2,  130.0,  127.2,  126.4, 124.4, 124.2, 117.7, 75.8, 39.0, 24.4"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"200.6","data":{"found":{"float_value":200.6,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-b4ed7a20eab53f680d31","name":"C10H9N · ORD FVVXWRGARUACNW-UHFFFAOYSA-N","smiles":"Cc1cc2ccccc2cn1","inchi":"InChI=1S/C10H9N/c1-8-6-9-4-2-3-5-10(9)7-11-8/h2-7H,1H3","formula":"C10H9N"},{"slug":"ord-compound-7a5ea1f0381bb40c0ab8","name":"C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N","smiles":"IC1COC1","inchi":"InChI=1S/C3H5IO/c4-3-1-5-2-3/h3H,1-2H2","formula":"C3H5IO"},{"slug":"ord-compound-55705f10a0dd8d75bdea","name":"C13H13NO · ORD HWZCJZPMSNGQDS-UHFFFAOYSA-N","smiles":"Cc1cc2ccccc2c(C2COC2)n1","inchi":"InChI=1S/C13H13NO/c1-9-6-10-4-2-3-5-12(10)13(14-9)11-7-15-8-11/h2-6,11H,7-8H2,1H3","formula":"C13H13NO"}],"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"]}