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

HRID 914927Notes

Reaction equation

HRID 914927 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)C=O.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 51%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.81 g 4-bromoanthranilic acid (J. Org. Chem. 1997, 62, 1240-1256), 39 mg 4-(dimethylamino)pyridine and 2.09 ml triethylamine in dry dimethylformamide is added dropwise 0.69 ml acetylchloride at 3° C. for 20 min. in an ice-water bath under argon. The reaction mixture is then heated at 90° C. for 3 h. and 1.08 g ammonium carbonate is added portionwise over 10 min., and the mixture is stirred at the same temperature for 1 h. After cooling, the mixture is poured onto 20 ml water and the precipitate is filtered, washed with water and dried in vacuo to give 0.46 g (51%) of crude 7-Bromo-2-methyl-3H-quinazolin-4-one as a light-brown solid. Mp. >191° C. (dec.). MS (EI): peaks at m/e: 240(M+, 100%), 223 (14%), 197(18%).

Workup

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

Sources & evidence

ORD record
ord-d880d0da84ae4a1cb5c67ce454799bce
Source dataset
uspto-grants-2007_09
Patent number
US07265125B2

Reaction notes

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