Acetic Anhydride → N-(5-Chloro-2-methyl-4-nitrophenyl)acetamide

HRID 506183Notes

Reaction equation

HRID 506183 reaction equation
[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[C:13](OC(=O)C)(=[O:15])[CH3:14]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH3:9])=[C:6]([NH:7][C:13](=[O:15])[CH3:14])[CH:8]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 837726-Chloro-4-nitro-o-toluidine

Product 1

HCID 304738N-(5-Chloro-2-methyl-4-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Chloro-2-methyl-4-nitroaniline was treated with acetic anhydride in the presence of 4-dimethylaminopyridine (DMAP) in CH2Cl2 to provide N-(5-chloro-2-methyl-4-nitrophenyl)acetamide, which was reacted with vinyl magnesium bromide at −40° C. to room temperature to give N-(7-chloro-4-methyl-1H-indol-5-yl)acetamide. Deprotection of the acetyl group by heating in an aqueous HCl solution at the reflux temperature provided 5-amino-7-chloro-4-methylindole.

Sources & evidence

ORD record
ord-0afb946d7146462898a1d73d08910c82
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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