Methyl 4-(cyclohexylamino)-3-nitrobenzoate → Methyl 3-amino-4-(cyclohexylamino)benzoate

HRID 968868Notes

Reaction equation

HRID 968868 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[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[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:6]([NH2:17])[CH:5]=1

Participants

4

Reactant 1

HCID 2972846Methyl 4-(cyclohexylamino)-3-nitrobenzoate

Product 1

HCID 4083987Methyl 3-amino-4-(cyclohexylamino)benzoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 50 (10.57 g, 37.9 mol) was hydrogenated in MeOH (130 mL) over 5% Pd/C (150 mg) under H2 for 30 minutes. The reaction was filtered through Celite and the solution was evaporated to give a brown solid (9.4 g, 99%). MS (ESI) 249.17 (M+H+).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. customthe solution was evaporated

Sources & evidence

ORD record
ord-24eb5018382e49dd92d20538c8e79af9
Source dataset
uspto-grants-2007_12
Patent number
US07304085B2

Reaction notes

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