Methyl {4-[(cyclohexylmethyl)amino]-3-nitrophenyl}carbamate → Methyl {3-amino-4-[(cyclohexylmethyl)amino]phenyl}carbamate

HRID 472933Notes

Reaction equation

HRID 472933 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:19])[O:17][CH3:18])=[CH:11][C:10]=2[N+:20]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[NH2:20][C:10]1[CH:11]=[C:12]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH:13]=[CH:14][C:9]=1[NH:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57591003Methyl {4-[(cyclohexylmethyl)amino]-3-nitrophenyl}carbamate

Product 1

HCID 57591006Methyl {3-amino-4-[(cyclohexylmethyl)amino]phenyl}carbamate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

Methyl {4-[(cyclohexylmethyl)amino]-3-nitrophenyl}carbamate (1.05 g, 3.42 mmol) was dissolved in 30 mL of EtOAc containing a catalytic amount of 10% Pd/C. The solution was shaken in a Parr hydrogenation apparatus under H2 atmosphere (40 psi) at rt overnight. The solution was filtered through Celite and the solvent evaporated. The product was directly used for the next step without further purification. Yield: 950 mg (99%). MS (ESI) (M−1-H)+ 277.9.

Workup

  1. filtrationThe solution was filtered through Celite
  2. customthe solvent evaporated
  3. customThe product was directly used for the next step without further purification

Sources & evidence

ORD record
ord-ad41b735935e4e56903ed6a011e626fb
Source dataset
uspto-grants-2014_01
Patent number
US08633235B2

Reaction notes

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