4-{[2-(acetylamino)ethyl]amino}-N,N-diethyl-3-nitrobenzamide → 4-{[2-(acetylamino)ethyl]amino}-3-amino-N,N-diethylbenzamide
Reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[CH:20]=[CH:19][C:11]([C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13])=[CH:10][C:9]=1[N+:21]([O-])=O)(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[CH:20]=[CH:19][C:11]([C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13])=[CH:10][C:9]=1[NH2:21])(=[O:3])[CH3:2]Participants
4
Procedure
Following general procedure 2C: A mixture of 4-{[2-(acetylamino)ethyl]amino}-N,N-diethyl-3-nitrobenzamide (0.150 g, 0.465 mmol) and 10% Pd/C in EtOAc (15 mL) was hydrogenated overnight at 40 psi. Usual work-up provided the title compound (0.164 g, 100%) which was used without further purification. 1H-NMR (CDCl3): δ 6.83 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 6.76 (d, J=2.0 Hz, 1H), 6.53 (d, J=8.4 Hz, 1H), 6.26 (br t, 1H), 3.53 (q, J=5.6 Hz, 2H), 3.43 (br s, 4H), 3.23 (t, J=5.6 Hz, 2H), 1.99 (s, 3H), 1.17 (t, J=6.4 Hz, 6H). MS (ESI) (M+H)+=293.
Sources & evidence
- ORD record
- ord-be0dd0f827f14d5a80ba33411e975900
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030139B2
Reaction notes
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