Ethyl 3-{4-[(diethylamino)carbonyl]-2-nitroanilino}propanoate → Ethyl 3-{2-amino-4-[(diethylamino)carbonyl]anilino}propanoate

HRID 1796456Notes

Reaction equation

HRID 1796456 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4]([C:6]1[CH:19]=[CH:18][C:9]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([N+:20]([O-])=O)[CH:7]=1)=[O:5])[CH3:2]>CCOC(C)=O.[Pd]>[NH2:20][C:8]1[CH:7]=[C:6]([C:4]([N:3]([CH2:23][CH3:24])[CH2:1][CH3:2])=[O:5])[CH:19]=[CH:18][C:9]=1[NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 22181355Ethyl 3-{4-[(diethylamino)carbonyl]-2-nitroanilino}propanoate

Product 1

HCID 22181324Ethyl 3-{2-amino-4-[(diethylamino)carbonyl]anilino}propanoateYield 115.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 2C: A mixture of ethyl 3-{4-[(diethylamino)carbonyl]-2-nitroanilino}propanoate (0.150 g, 0.445 mmol) and 10% Pd/C in EtOAc (15 mL) was hydrogenated overnight at 40 psi. Usual work-up provided the title compound (0.158 g) which was used without further purification. 1H-NMR (CDCl3): δ 6.86 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 6.80 (d, J=2.0 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 4.18 (q, J=7.2 Hz, 2H), 3.46 (t and overlapping br s, J=5.6 Hz, 6H), 2.66 (t, J=6.8 Hz, 2H), 1.28 (t, J=7.2 Hz, 3H), 1.18 (t, J=6.8 Hz, 6H). MS (ESI) (M+H)+=308.

Sources & evidence

ORD record
ord-892dcaaaaeeb4e7dbcea268459f45119
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

Loading…