Carbon Dioxide → 4(3H)-Quinazolinone, 3-(2-methylphenyl)-2-(2-oxopropyl)-

To a magnetically stirred solution of 5 mmol of LDA, prepared by mixing 2.1 ml (5 mmol) of n-butyllithium (2.4 M) and 0.71 g (7 mmol) of diisopropylamine in 25 ml of dy THF at 0° under nitrogen, was added 1.25 g (5 mmol) of methaqualone. After 30 minutes, the entire solution of lithio salt was transferred via syringe (50 ml) to an addition funnel which was attached to a three-necked 100 ml flask. The bottom half of the additional funnel was loosely enclosed in aluminum foil which formed a cup that held several small pieces of dry ice. To a solution of 4.40 g (50 mmol) of ethyl acetate in 60 ml of dry THF at 0°, was added dropwise the 5 mmol solution of lithio salt over a 65 minute period. After addition was complete, the clear yellow solution was poured into 100 ml of water containing 10 ml of 1 N NCl. The resulting solution was extracted twice with 200 ml portions of ether, which were combined, dried and concentrated. TLC analysis (ether-acetone, 98:2) revealed two spots, with methaqualone as the major component. Column chromatography afforded, on elution with hexane-ether (9:1), 0.14 g (8%) of 2-acetonyl-3-o-tolyl-4(3H)-quinazolinone (III n) as white crystals, mp 164°-165.6°. The 1H NMR spectrum was identical with samples prepared by the general sodium hydride acylation procedure described subsequently.

1. customthe entire solution of lithio salt was transferred via syringe
2. custom(50 ml) to an addition funnel which was attached to a three-necked 100 ml flask
3. customformed a cup that
4. additionAfter addition
5. extractionThe resulting solution was extracted twice with 200 ml portions of ether, which
6. customdried
7. concentrationconcentrated

ORD record

ord-e9f66410ff5d4c9b909870abbcbd496b

Source dataset

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04183931