2-nitro-N-isopropyl-5-phenoxybenzamide → 2-amino-N-isopropyl-5-phenoxybenzamide

HRID 2099966Notes

Reaction equation

HRID 2099966 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:5]=1[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])=[O:7])([O-])=O>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:5]=1[C:6]([NH:8][CH:9]([CH3:10])[CH3:11])=[O:7]

Participants

4

Reactant 1

HCID 577968982-nitro-N-isopropyl-5-phenoxybenzamide

Product 1

HCID 577968942-amino-N-isopropyl-5-phenoxybenzamideYield 99.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 34B (710 mg, 2.37 mmol) in MeOH (8 mL) was treated with 20% palladium hydroxide on carbon (110 mg). The resulting slurry was stirred under a hydrogen atmosphere for 4 hours, and then filtered through a 0.4 μm polycarbonate membrane to remove the catalyst. The filtrate was concentrated to give 34C as a white solid (636 mg, 99%).

Workup

  1. filtrationfiltered through a 0.4 μm polycarbonate membrane
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3fd0ee64b66c4f269b0a05a7fb26adca
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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