Hydrochloric Acid → HCID 178441852, compound

Participants

Reaction Steps

Preparation D11, Step 1: 2-amino-5-(trifluoromethyl)-benzamide (100 mg, 0.49 mmol, 1 eq) was suspended in THF (5 mL) at 0° C. then 1.000N NaOH (0.73 mL, 0.735 mmol, 1.5 eq) was added. Valeryl chloride (87 μL, 0.735 mmol, 1.5 eq) was slowly dripped into the mixture. After 4 hours, little reaction. Added more 1.000N NaOH (5.84 mL, 5.88 mmol, 12 eq) followed by more valeryl chloride (0.70 mL, 5.88 mmol, 12 eq). After the reaction was complete, added conc. HCl until pH=3. Stripped off the THF. Extracted the aqueous 3 times with ethyl acetate. The organic layers were combined, dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate to give 2-butyl-6-(trifluoromethyl)quinazolin-4-ol (110 mg) as a white solid. Yield=78%. LCMS detects (M+H)+=271.21.

Provenance & Evidence