4(3H)-Quinazolinone, 3-(2-chlorophenyl)-6-fluoro-2-methyl- → 3-(2-Chloro-phenyl)-6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one

HRID 897039

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH3:20].CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH:20]=[CH:23][N:24]([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 3-(2-chloro-phenyl)-6-fluoro-2-methyl-3,4-dihydro-quinazolin-4-one (1.0 g, 3.46 mmol) and dimethylformamide dimethyl acetal (0.92 mL, 6.92 mmol) in dimethylformamide (4 mL) was heated to 140° C. for 24 hours. The reaction was cooled to ambient temperature and concentrated at reduced pressure. The dark residue was triturated with methanol and the bright yellow crystalline solid which formed was collected and dried to give 1.075 g (90%) of 3-(2-chloro-phenyl)-6-fluoro-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one which had: mp 210-211° C.; 1H NMR δ 7.86 (d, J=12.3 Hz, 1 H), 7.79 (dd, J=3, 8.5 Hz, 1 H), 7.61-7.54 (m, 1 H), 7.51-7.29 (m, 5 H), 4.06 (d, J=12.3 Hz, 1 H), 2.80 (br s, 6 H). Analysis calculated for C18H15ClFN3O: C, 62.89; H, 4.40; N, 12.22. Found: C, 62.75; H, 4.28; N, 12.29.

Workup

temperatureThe reaction was cooled to ambient temperature
concentrationconcentrated at reduced pressure
customThe dark residue was triturated with methanol
customthe bright yellow crystalline solid which formed
customwas collected
customdried

Sources & evidence

ORD record: ord-bc3b02814dc0452c87080d478d366964
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921764B2

Linked notes

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