5-Methoxy-2-nitrobenzamide → 2-Amino-5-methoxybenzamide

HRID 606482Notes

Reaction equation

HRID 606482 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-])=O)=[C:7]([CH:11]=1)[C:8]([NH2:10])=[O:9]>CO.[C].[Pd]>[NH2:12][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:7]=1[C:8]([NH2:10])=[O:9]

Participants

4

Reactant 1

HCID 184039495-Methoxy-2-nitrobenzamide

Product 1

HCID 203382172-Amino-5-methoxybenzamideYield 99.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-methoxy-2-nitrobenzamide (9.70 g, 49.4 mmol) in methanol (250 mL) was added 10% palladium carbon (2.00 g), and the mixture was stirred under hydrogen atmosphere (1 atm) at room temperature for 6 hr. The insoluble material was filtered off, and the filtrate was concentrated to give 2-amino-5-methoxybenzamide as a pale-yellow powder (8.20 g, 99%).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-924584551a8d4e2598d20dfe98855391
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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