N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl}acetamide → N-{3-amino-4-[(cyclohexylmethyl)amino]phenyl}acetamide

HRID 472939Notes

Reaction equation

HRID 472939 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][C:10]=2[N+:19]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.[Pd]>[NH2:19][C:10]1[CH:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[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 57591007N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl}acetamide

Product 1

HCID 57591000N-{3-amino-4-[(cyclohexylmethyl)amino]phenyl}acetamideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The above crude product N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl}acetamide (6.60 g) was hydrogenated in ethyl acetate (300 mL) catalyzed by 10% Pd/C (0.5 g) at 20-30 psi H2 in Parr shaker for 4.5 h at room temperature. After filtration through celite and concentration, 5.08 g (97%) of a purple solid was obtained. which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 1.00 (m, 2H), 1.24 (m, 3H), 1.59 (m, 2H), 1.72 (m, 2H), 1.84 (m, 2H), 2.13 (s, 3H), 2.91 (d, J=6.64 Hz, 2H), 3.37 (s broad, 3H), 6.56 (d, J=8.40 Hz, 1H), 6.69 (dd, J=8.30, 2.25 Hz, 1H), 6.98 (s, 1H), 7.12 (d, J=2.34 Hz, 1H). MS (ESI) (M+H)+: 262.31.

Workup

  1. filtrationAfter filtration
  2. concentrationthrough celite and concentration

Sources & evidence

ORD record
ord-9a501e9b619248a086feedca9f724875
Source dataset
uspto-grants-2014_01
Patent number
US08633235B2

Reaction notes

Loading…