Acetic Acid → 6-bromo-7-methylquinazolin-4(3H)-one

HRID 2092306Notes

Reaction equation

HRID 2092306 reaction equation
CO.C(O)(=O)C.[CH3:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:18])[NH:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1.[Br:19]Br>>[Br:19][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:8]=1[CH3:7])[N:15]=[CH:14][NH:13][C:12]2=[O:18]

Participants

5

Reactant 4

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

Product 1

HCID 1357422976-bromo-7-methylquinazolin-4(3H)-one

Procedure

To a round-bottomed flask were added methanol (70 ml, 91 mmol), glacial acetic acid (70 ml, 1212 mmol), and 7-methylquinazolin-4(3H)-one (14.56 g, 91 mmol). The reaction mixture was stirred at room temperature for 5 min followed by the slow addition of bromine (9.3 ml, 182 mmol). The reaction was stirred at room temperature for 3 h. Volatiles were evaporated under reduced pressure and the resulting crude residue washed with aqueous sodium thiosulfate to remove excess bromine and HBr, then oven dried to afford 6-bromo-7-methylquinazolin-4(3H)-one as light yellow amorphous solid. MS (M+H)+ 239, 241.

Workup

  1. stirringThe reaction was stirred at room temperature for 3 h
  2. customVolatiles were evaporated under reduced pressure
  3. washthe resulting crude residue washed with aqueous sodium thiosulfate
  4. customto remove excess bromine and HBr
  5. customoven dried

Sources & evidence

ORD record
ord-81c8b4de0f4340f1a8175a49dd185b2f
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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