Ammonia → 6-Bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 1048873Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[C:6]([C:19](OCC)=[O:20])[C:5]2=[O:24].[NH3:25]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[C:6]([C:19]([NH2:25])=[O:20])[C:5]2=[O:24]

Participants

Conditions

Temperature: 150 °C

Procedure

Compound D (1.00 g, 2.56 mmol, 1.00 eq) was suspended in 7N ammonia in methanol (30 mL) in a microwave vial and the reaction was heated in a microwave reactor at 150° C. for 60 minutes. The reaction was concentrated to afford 881 mg (95%) of the title compound as a brown solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.08 (d, J=4.0 Hz, 1H), 8.57 (s, 1H), 8.43 (d, J=2.4 Hz, 1H), 7.85 (dd, J=9.1, 2.4 Hz, 1H), 7.77-7.73 (m, 2H), 7.66 (d, J=4.1 Hz, 1H), 7.56-7.50 (m, 2H), 7.02 (d, J=9.1 Hz, 1H); ES-MS [M+1]+: 361.2.

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-70292c5a318f41d6b7ea7bb320b05834
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382208B1

Reaction notes

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