Tert-Butyl nitrite → 2-Chloro-6,7-dihydro-5H-quinazolin-8-one oxime

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5,6,7,8-tetrahydro-quinazoline (Eur. J. Med. Chem. 1982, 17, 75)(1.0 g; 5.9 mmol) is dissolved in THF (80 ml) and cooled to −78° C. KOtBu (667 mg; 5.9 mmol) in THF (10 ml) is added dropwise and stirred for 5 minutes after complete addition. t-Butyl nitrite (2 ml; 27.8 mmol) is added to the orange solution and the reaction mixture warmed to room temperature. After 10 minutes the reaction mixture is poured on water/HOAc (800/1 ml) and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to deliver the title compound as yellow-orange crystals (1.1 g; 95%).

Provenance & Evidence