Acetic Acid → 5-bromo-7-methylquinazolin-4(3H)-one
Reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CO.CC(O)=O.[Br:19]Br>>[Br:19][C:4]1[CH:3]=[C:2]([CH3:1])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:12])[NH:7][CH:8]=[N:9]2Participants
5
Procedure
To a solution of 7-methylquinazolin-4(3H)-one (900 mg, 5.63 mmol) in MeOH (180 mg, 5.63 mmol) and AcOH (5.07 g, 84.45 mmol) was added bromine (300 μL, 5.63 mmol) and the reaction mixture was stirred at rt for 4 h. Then the reaction mixture was quenched with an aq. solution of sodium thiosulphate. The precipitate obtained was filtered and dried to afford 900 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 12.24 (br s, 1H), 8.18 (s, 1H), 8.08 (s, 1H), 7.66 (s, 1H), 2.48 (s, 3H).
Workup
- customThen the reaction mixture was quenched with an aq. solution of sodium thiosulphate
- customThe precipitate obtained
- filtrationwas filtered
- customdried
Sources & evidence
- ORD record
- ord-bb17728b65a34f65a65c3a1a9155ae1a
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006257B2
Reaction notes
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