Formamide → 6-Bromo-7-methoxy-3,4-dihydroquinazolin-4-one

HRID 240990Notes

Reaction equation

HRID 240990 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([Br:14])=[CH:8][C:3]=1[C:4](OC)=[O:5].C([O-])=O.[NH4+].O.[CH:20]([NH2:22])=O>>[Br:14][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][C:10]=1[O:12][CH3:13])[N:1]=[CH:20][NH:22][C:4]2=[O:5]

Participants

5

Reactant 4

HCID 713FormamideHCID 962WaterHCID 2723923Ammonium formateHCID 19701951Methyl 2-amino-5-bromo-4-methoxybenzoate

Product 1

HCID 1357423626-Bromo-7-methoxy-3,4-dihydroquinazolin-4-oneYield 72%

Procedure

A solution of methyl 2-amino-5-bromo-4-methoxybenzoate (75 mg, 0.29 mmol) and ammonium formate (38 mg, 0.8 mmol) in formamide (1 mL) was heated at 165° C. for 18 h. The mixture was allowed to cool to room temperature then diluted with an excess of water. The solid formed was collected by filtration and washed with water then ethyl acetate and dried to give 6-bromo-7-methoxyquinazolin-4(3H)-one (53 mg, 72% yield) as a pale yellow solid. MS (EI) for C9H7BrN2O2: 255, 257 (MH+).

Workup

  1. customThe solid formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. dry with materialethyl acetate and dried

Sources & evidence

ORD record
ord-73ca71c0d0ae43eb9b3db199c5b2e893
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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