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

HRID 1783890Notes

Reaction equation

HRID 1783890 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 was evaporated. The product was directly used in the next step without further purification. Yield: 950 mg (99%). MS (ESI) (M+H)+: 277.9.

Workup

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

Sources & evidence

ORD record
ord-e6bcad80cf7741f689703833b32c99fb
Source dataset
uspto-grants-2009_03
Patent number
US07501447B2

Reaction notes

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