Acetic Acid → 5-bromo-7-methylquinazolin-4(3H)-one

HRID 1469759Notes

Reaction equation

HRID 1469759 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]2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 24408BromineHCID 1354525337-Methyl-4(3H)-quinazolinone

Product 1

HCID 1363368235-bromo-7-methylquinazolin-4(3H)-oneYield 66.9%

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

  1. customThen the reaction mixture was quenched with an aq. solution of sodium thiosulphate
  2. customThe precipitate obtained
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-bb17728b65a34f65a65c3a1a9155ae1a
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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