Methyl 2-(acetylamino)-5-nitro-4-(trifluoromethyl)benzoate → Methyl 2-acetamido-5-amino-4-(trifluoromethyl)benzoate

HRID 2069262Notes

Reaction equation

HRID 2069262 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 58964493Methyl 2-(acetylamino)-5-nitro-4-(trifluoromethyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58964516Methyl 2-acetamido-5-amino-4-(trifluoromethyl)benzoateYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.7 g (5.55 mmol) of 2-acetylamino-5-nitro-4-trifluoromethyl-benzoic acid methyl ester in 29 ml of methanol is treated with 250 mg of Pd/C (10%) and the mixture stirred under 5 bars of hydrogen for 20 minutes. The mixture is filtered and the filtrate concentrated in vacuo to give 1.58 g (quantitative) of 2-acetylamino-5-amino-4-trifluoromethyl-benzoic acid methyl ester as yellow crystals, m.p. 143-152° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d9f3206da0324822a5c3b3d8f56a9006
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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