Hydrochloric Acid → HCID 86626313, compound

Participants

Reaction Steps

To a solution of 7-amino-4-(4-fluorophenyl)-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 15, 50 mg) in acetic acid (465 μL)/concentrated hydrochloric acid (570 μL) was added a solution of sodium nitrite (13.3 mg) in water (115 μL) under ice-cooling, and the mixture was stirred at the same temperature for 1.5 hours. To the reaction mixture was added a mixture of sodium hydrogen sulfite (182 mg), copper(II) chloride (23.5 mg), acetic acid (225 μL) and concentrated hydrochloric acid (115 μL) at the same temperature, and the mixture was stirred at room temperature for 2 hours. After ice-cooling, the reaction mixture was gradually poured to water with ice (15 mL) and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated in vacuo to give crude 4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-sulfonyl chloride.

Provenance & Evidence