{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-98336091cd12456389bc47ef2d32dae4","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"8dbe2e6d3fb8ba8462ce07eac31fd587da8ddd86c7c63613e7c9850c128029b0","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-98336091cd12456389bc47ef2d32dae4-fe9aed6d0579","ord-98336091cd12456389bc47ef2d32dae4-aaa84acf0f87"],"reactant_slugs":["ord-compound-e047a7dab2e6d893e7e6","ord-compound-c548c24d29328ab9f616"],"product_slugs":["ord-compound-f4ed1187d755234e9778"],"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_114"},{"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":6,"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":9,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=2C=CC=CC2C=CC1C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"91-63-4"}],"amount":{"moles":{"value":3,"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":1.8,"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":18,"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":1.8,"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":28.2,"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;  0.86  mL,  9.0  mmol) was added to a stirred solution of quinaldine 1b (400 mg, 3.0 mmol), concentrated H2SO4 (298 μL,  6.0  mmol),  1-Boc-3-(iodo)azetidine  (1.58  g,  3.0  mmol)  and  iron(II)  sulfate  heptahydrate  (200  mg,  0.8  mmol)  in  DMSO  (30  mL)  at  room  temperature.  After  30  min  a  further  portion  of  iron(II)  sulfate  heptahydrate  (200  mg,  0.8  mmol)  and  H2O2  (30%  in  H2O;  0.86  mL,  9.0  mmol)  was  added  and  the  mixture  was  stirred  at  room  temperature  for  30  min.  Further  H2O2  (0.86  mL,  9.0  mmol)  and  iron(II)  sulfate  heptahydrate  (200  mg,  0.8  mmol)  was  added,  and  the  mixture  was  stirred  for  120  min,  then  poured  into  an  ice-cold  solution  of  NaOH  and  adjusted  to  pH  >10.  The  aqueous  was  extracted  with  Et2O.  The  aqueous  layer  was  then  saturated  with  solid  NaCl,  and  extracted  with  CHCl3  until  all  the  product  was  removed  from  the  aqueous  layer.  The  combined  organic  extracts  were  dried  (MgSO4), filtered  and  the  solvent  removed  under  vacuum  to  leave  a  crude  residue.  The  residue  was  purified  by  column  chromatography  on  silica  gel  using  EtOAc  /  hexanes  (1:1  to  1:0)  as  eluent  to  give  the  desired  product 3b (450 mg, 50%) as an oil that crystallized on standing."},"outcomes":[{"reaction_time":{"value":1,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)N1CC(C2=CC(=NC=3C=CC=CC32)C)C1"},{"type":"CAS_NUMBER","value":"1180653-83-1"}],"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":50}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ 8.07 (d, J = 8.3 Hz, 1H), 7.70-7.67 (q, J = 7.4 Hz, 2H), 7.51 (t, J = 7.5 Hz, 1H), 7.28 (s, 1H), 4.49 (t, J = 8.2 Hz, 2H),  4.44-4.38  (m,  1H),  4.17  (br.  s,  2H),  2.77  (s,  3H),  1.46  (s,  9H);  13C  NMR  (100  MHz;  CDCl3) δ - 13 -159.0, 156.4, 148.1, 146.8, 129.8, 129.5, 126.1, 125.0, 122.8, 118.9, 80.0, 54.1, 30.1, 28.5, 25.6"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"299.0","data":{"found":{"float_value":299,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-e047a7dab2e6d893e7e6","name":"C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N","smiles":"Cc1ccc2ccccc2n1","inchi":"InChI=1S/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3","formula":"C10H9N"},{"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-f4ed1187d755234e9778","name":"C18H22N2O2 · ORD UZRFQQVRHMBUIL-UHFFFAOYSA-N","smiles":"Cc1cc(C2CN(C(=O)OC(C)(C)C)C2)c2ccccc2n1","inchi":"InChI=1S/C18H22N2O2/c1-12-9-15(14-7-5-6-8-16(14)19-12)13-10-20(11-13)17(21)22-18(2,3)4/h5-9,13H,10-11H2,1-4H3","formula":"C18H22N2O2"}],"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"]}