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

HRID 392973Notes

Reaction equation

HRID 392973 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=2[N+:18]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.C(OCC)(=O)C.[Pd]>[NH2:18][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 1

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

Product 1

HCID 4083987Methyl 3-amino-4-(cyclohexylamino)benzoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 45 (2.03 g, 7.29 mmol) in a mixture of methanol (25 mL) and ethyl acetate (25 mL) was hydrogenated over 10% palladium on carbon (0.20 g) at 25 psi for 15 h. The reaction mixture was filtered and concentrated to afford compound 46 as a crude grey-brown oil (1.99 g, 100%). ESI-MS m/e 249.3 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8e472f9e36424b86b116422fe0899506
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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