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

HRID 1750245Notes

Reaction equation

HRID 1750245 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH3:16])=[C:6]([N+:17]([O-])=O)[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH3:16])=[C:6]([NH2:17])[CH:5]=1

Participants

4

Reactant 1

HCID 867144524-(2-Methyl-cyclopentylamino)-3-nitro-benzoic acid methyl ester

Product 1

HCID 632795193-Amino-4-(2-methyl-cyclopentylamino)-benzoic acid methyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

12.74 g 4-(2-Methyl-cyclopentylamino)-3-nitro-benzoic acid methyl ester were dissolved in 80 ml methanol, 0.39 g of palladium on carbon (10%) were added and the mixture was hydrogenated at 5 bar for 16 h. The catalyst was removed by filtration over celite, the filtrate was concentrated and the residue purified by chromatography (silica, ethyl acetate/hexane) to obtain 8.17 g (72%) of 3-Amino-4-(2-methyl-cyclopentylamino)-benzoic acid methyl ester.

Workup

  1. customThe catalyst was removed by filtration over celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue purified by chromatography (silica, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-886a0c25bf07421f8010258f6828082f
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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