Benzyl Alcohol → 7-(Benzyloxy)-3,4-dihydroquinazolin-4-one

HRID 639963Notes

Reaction equation

[Na].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1.Cl>O>[CH2:2]([O:9][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium (10.3 g, 0.45 mol) was added to benzyl alcohol (200 ml, 1.94 mol) under argon and the mixture heated at 120° C. for 4 hours. 7-Fluoroquinazolin-4-(3H)-one (15 g, 90 mmol) was added to the mixture and the reaction heated at 120° C. for 18 hours. The mixture was cooled, poured into water (800 ml) and the pH adjusted to 4 with hydrochloric acid (2 N, 150 ml). The resultant precipitate was collected by filtration, washed with water, pentane and diethyl ether to yield 7-(benzyloxy)quinazolin-4-(3H)-one (22.3 g, 98% yield):

Workup

temperaturethe reaction heated at 120° C. for 18 hours
temperatureThe mixture was cooled
filtrationThe resultant precipitate was collected by filtration
washwashed with water, pentane and diethyl ether

Sources & evidence

ORD record: ord-9d78a28cf6a74683938bf338d100f832
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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