Hydrochloric Acid → Ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate

HRID 625797Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4]([O:6]C)=O.[C:13]([C:18]#[N:19])(=[O:17])[O:14][CH2:15][CH3:16].Cl>CC(O)=O>[F:12][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][CH:10]=1)[N:1]=[C:18]([C:13]([O:14][CH2:15][CH3:16])=[O:17])[NH:19][C:4]2=[O:6]

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred mixture of methyl 2-amino-5-fluorobenzoate (1 g, 5.92 mmol) and ethyl carbonocyanidate (1.17 g, 11.8 mmol) in HOAc (8 mL) was treated with a 12 N aq solution of hydrochloric acid (0.8 mL). The resulting mixture was heated at 70° C. for 3 h. After cooling to rt, the solvent was removed under reduced pressure. The residue was suspended in water and treated with a saturated aq solution of NaHCO3 until pH=7. The solid was filtered, washed with water/diethyl ether and dried under reduced pressure to afford ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate (1.2 g, 86%). 1H NMR (300 MHz, DMSO-d6) δ 12.79 (s, 1H), 7.76-7.95 (m, 3H), 4.39 (q, J=7.0 Hz, 2H), 1.36 (t, J=7.0 Hz, 3H); LC-MS (ESI) m/z 237 (M+H)+.

Workup

temperatureAfter cooling to rt
customthe solvent was removed under reduced pressure
additiontreated with a saturated aq solution of NaHCO3 until pH=7
filtrationThe solid was filtered
washwashed with water/diethyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-a8734cc182f049ad8b18dc71aaf2d385
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09308207B2

Reaction notes

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