6-Nitro-3,4-dihydroquinazolin-4-one → 6-Amino-3,4-dihydroquinazolin-4-one

HRID 1696560Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=[O:14])([O-])=O>CO.C1COCC1.CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=[O:14]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 6-nitroquinazolin-4(3H)-one (4.15 g, 21.7 mmol) and 10% Pd/C (0.3 g) in MeOH (25 mL) and THF (50 mL) was stirred under H2 (1 atm) at 40° C. for 18 h. The mixture was diluted with DMF (50 mL), stirred overnight under H2, then placed under an Ar atmosphere. After the addition of Pd/C (0.4 g), the mixture was placed under an H2 atmosphere and warmed to 50° C. and stirred for 4 h. The reaction mixture was filtered through Celite®, washed with warm DMF (75 mL) and the combined filtrates evaporated to yield 6-aminoquinazolin-4(3H)-one (3.10 g, 88% yield) as a yellow solid. MS (ESI) m/e (M+H+) 162.3

Workup

stirringstirred overnight under H2
temperaturewarmed to 50° C.
stirringstirred for 4 h
filtrationThe reaction mixture was filtered through Celite®
washwashed with warm DMF (75 mL)
customthe combined filtrates evaporated

Sources & evidence

ORD record: ord-82824f5c73544803b39ecd93f962c5b5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163756B2

Reaction notes

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