4-(Methoxycarbonyl)-2-nitrobenzoic acid → 2-Amino-4-(methoxycarbonyl)benzoic acid

HRID 1736375Notes

Reaction equation

HRID 1736375 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[N+:14]([O-])=O)([OH:3])=[O:2]>C(O)C.[C].[Pd]>[NH2:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[C:1]([OH:3])=[O:2])[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 219064744-(Methoxycarbonyl)-2-nitrobenzoic acid

Product 1

HCID 133493862-Amino-4-(methoxycarbonyl)benzoic acidYield 65.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 4-carboxy-3-nitrobenzoate (3 g, 13.3 mM) in ethanol (20 ml) was hydrogenated at atmospheric pressure in the presence of 10% palladium-carbon (1 g) for 40 minutes. After filtration of the catalyst, the solid was recrystallised from ethanol to give methyl 3-amino-4-carboxybenzoate (1.7 g, 65%).

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-0706760626d84f33bc986c666f3f9c1a
Source dataset
uspto-grants-1996_07
Patent number
US05541178

Reaction notes

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