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

HRID 1796455Notes

Reaction equation

[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[NH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CCO>[CH2:1]([N:3]([CH2:16][CH3:17])[C:4]([C:5]1[CH:10]=[CH:9][C:8]([NH:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)=[O:15])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Following general procedure 2B: A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (0.200 g, 0.833 mmol), ethyl 3-aminopropanoate (0.116 g, 0.757 mmol) in 80% aq. EtOH (5 mL) was heated at 90° C. overnight. After work-up, the crude product was purified by silica gel column chromatography (50% EtOAc/Hexanes to 100% EtOAc) to provide the title compound (0.162 g, 63%). 1H-NMR (CDCl3): δ 8.34 (br t, J=5.6 Hz, 1H), 8.29 (d, J=2.0 Hz, 1H), 7.58 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 6.92 (d, J=9.2 Hz, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.69 (q, J=6.4 Hz, 2H), 3.44 (br s, 4H), 2.72 (t, J=6.4 Hz, 2H), 1.30 (t, J=6.4 Hz, 3H), 1.22 (t, J=6.8 Hz, 6H). MS (ESI) (M+H)+=338.

Workup

customAfter work-up, the crude product was purified by silica gel column chromatography (50% EtOAc/Hexanes to 100% EtOAc)

Sources & evidence

ORD record: ord-3d6d43b96a0a4a26b81248ba0329f890
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030139B2

Reaction notes

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