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

HRID 1750224Notes

Reaction equation

HRID 1750224 reaction equation
[CH3:1][O:2][C:3](=[O:21])[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[CH3:17])=[C:6]([N+:18]([O-])=O)[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:21])[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[CH3:17])=[C:6]([NH2:18])[CH:5]=1

Participants

4

Reactant 1

HCID 867144344-(2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester

Product 1

HCID 613065513-Amino-4-(2-methyl-cyclohexylamino)-benzoic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

13.50 g 4-(2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester were dissolved in 60 ml methanol, 0.49 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 12.00 g (99%) of 3-Amino-4-(2-methyl-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-1253ce7b9f084ac986d79a1fbc023d66
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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