4-((1R,2R)-2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester → 3-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl ester

HRID 1750230Notes

Reaction equation

HRID 1750230 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[CH3:17])=[C:6]([N+:18]([O-])=O)[CH:5]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[CH3:17])=[C:6]([NH2:18])[CH:5]=1

Participants

4

Reactant 1

HCID 867144374-((1R,2R)-2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester

Product 1

HCID 867144383-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9.27 g 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-nitro-benzoic acid methyl ester were dissolved in 100 ml ethanol, 0.20 g of palladium on carbon (10%) were added and the mixture was hydrogenated at 5 bar for 3 h. The catalyst was removed by filtration over celite, the filtrate was concentrated to obtain 8.20 g (99%) of 3-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl ester. C15H22N2O2 (262.35), LCMS (method 8—1—1): Rt=0.77 min, m/z=263.15 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-bbfc60c13cad44f9bb853a69b4ed35f1
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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