4-(2-Ethyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester → 3-Amino-4-(2-ethyl-cyclohexylamino)-benzoic acid methyl ester

HRID 1750249Notes

Reaction equation

HRID 1750249 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[CH2:17][CH3:18])=[C:6]([N+:19]([O-])=O)[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[CH2:17][CH3:18])=[C:6]([NH2:19])[CH:5]=1

Participants

4

Reactant 1

HCID 867144554-(2-Ethyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester

Product 1

HCID 614680353-Amino-4-(2-ethyl-cyclohexylamino)-benzoic acid methyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.45 g 4-(2-Ethyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester were dissolved in 60 ml methanol, 0.02 g of palladium on carbon (10%) were added and the mixture was hydrogenated at 5 bar for 4 h. The catalyst was removed by filtration over celite, the filtrate was concentrated to obtain 0.40 g (100%) of 3-Amino-4-(2-ethyl-cyclohexylamino)-benzoic acid methyl ester.

Workup

  1. customThe catalyst was removed by filtration over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6296d352ad5c4c9b99656576ec1ce083
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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