2-Aminobenzophenone → HCID 21518534, compound

HRID 1283616Notes

Reaction equation

HRID 1283616 reaction equation
NC1C=CC=CC=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C([O:20]Cl)(C)(C)C.[CH3:22][S:23][CH2:24][C:25](OCC)=[O:26]>C(Cl)Cl>[C:4]([O:5][C:25](=[O:26])[CH2:24][S:23][CH3:22])(=[O:20])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 760802-AminobenzophenoneHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 21518534HCID 21518534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In process (c) a solution of a selected aminobenzophenone (X) in a halogenated organic solvent, e.g., methylene chloride, is treated at -50° to -78°C. with t-butylhypochlorite and then with a lower alkyl α-(methylthio)acetate as, for example, ethyl α-(methylthio)acetate to give an ethyl 2-amino-3-(5- or 7-) benzoyl-α-(methylthio)acetate (XI) which can be isolated or can be converted in situ by the addition of a dilute mineral acid such as dilute hydrochloric acid to a 3-methylthio-4-(5- or 7-) benzolindolin-2-one (XII). The 3-methylthio group is removed by stirring a dry tetrahydrofuran solution of the 3-methylthio compound (XII) with Raney-Ni under an inert gas to give a benzoylindolin-2-one of Formula I.

Sources & evidence

ORD record
ord-7a1fb40ca74c40a8a025b6b4e37af77e
Source dataset
uspto-grants-1976_08
Patent number
US03975531

Reaction notes

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