Acetyl chloride → 7-Bromo-2-methylquinazolin-4(3H)-one

HRID 1271216Notes

Reaction equation

HRID 1271216 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[CH2:12]([N:14](CC)CC)[CH3:13].C(Cl)(=O)C.C(=O)([O-])[O-].[NH4+].[NH4+]>CN(C)C1C=CN=CC=1.CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:8])[NH:14][C:12]([CH3:13])=[N:11]2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 886912-Amino-4-bromobenzoic acidHCID 517111Ammonium Carbonate

Product 1

HCID 1358045037-Bromo-2-methylquinazolin-4(3H)-oneYield 99.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1 g (4.63 mmol) 4-bromoanthranilic acid (J. Org. Chem. 1997, 62, 1240–1256), 50 mg (0.417 mmol) of 4-(dimethylamino)pyridine and 2.58 ml (18.5 mml) of triethylamine in dry DMF (5 ml) was added dropwise 0.79 ml (11.1 mmol) of acetylchloride at 3° C. for 20 min. in an ice-water bath under argon. The reaction mixture was heated at 90° C. for 3 h. and 1.32 g (13.89 mmol) of ammonium carbonate were added portionwise over 10 min., and the mixture was stirred at the same temperature for 1 h. After cooling, the mixture was poured into water and the precipitate filtered, washed with water and dried in vacuo to give 1.1 g (99.4%) of 7-bromo-2-methyl-3H-quinazolin-4-one as a light-brown solid. Mp. >191° C. (dec.). EI mass spectrum, m/e: 240 (M calculated for C9H7BrN2O: 240).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-332b4648714846c7a3306d75829fe008
Source dataset
uspto-grants-2007_04
Patent number
US07205309B2

Reaction notes

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