N-(2-Chloro-5-nitrophenyl)-4,4-dimethyl-3-oxopentanamide → 2-Chloro-5-nitroaniline

HRID 1379806Notes

Reaction equation

HRID 1379806 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11]C(=O)CC(=O)C(C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11]

Participants

3

Reactant 1

HCID 96110N-(2-Chloro-5-nitrophenyl)-4,4-dimethyl-3-oxopentanamide

Product 1

HCID 226912-Chloro-5-nitroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride, was dissolved 2.9 g (0.01 mol) of N-(2-chloro-5-nitrophenyl)-α-pivaloylacetic acid amide, which is easily obtained by a reaction of 2-chloro-5-nitroaniline with pivaloylacetic acid ester; and then to this was added, slowly, 1.50 g (0.00525 mol) of 1,3-dibromo-5,5-dimethylhydantoin, on an ice bath, followed by stirring for 1 hour.

Sources & evidence

ORD record
ord-f6e812af60894969bb758c967cec0c19
Source dataset
uspto-grants-1997_09
Patent number
US05672714

Reaction notes

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