Sodium Hydroxide → HCID 10659340, compound

Participants

Reaction Steps

Aluminum hydride (0.6M in THF, 80 ml) is added to 3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxalin-4-one (XXXV, EXAMPLE 246, 3.21 g) and the resulting solution is heated at reflux for 36 hr. After 24 hr, lithium aluminum hydride (600 mg) is added as starting material is still present After cooling to 20°-25°, methanol (12.1 ml) and sodium hydroxide (6N, 50.0 ml) are added successively and the resultant solution stirred for 30 min at 20°-25°. Aqueous workup (ethyl acetate, magnesium sulfate) and purification by flash chromatography eluting with hexane/ethyl acetate (2/1), pooling the appropriate fractions and concentration gives the title compound, IR (mineral oil) 3381, 2924, 1511, 1492, 1290, 1231, 838 and 741 cm-1 ; NMR (CDCl3) 8.04, 7.58, 7.42, 7.0-7.2, 6.8-6.95, 4.66 and 4.07 δ; MS (m/z) 265, 264, 237, 144 and 118.

Provenance & Evidence