N-Methylformamide → 7-Bromo-3-methyl-3,4-dihydroquinazolin-4-one

HRID 1619293Notes

Reaction equation

HRID 1619293 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[CH3:14][NH:15][CH:16]=O>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[N:15]([CH3:16])[CH:14]=[N:11]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 31254N-MethylformamideHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 585745147-Bromo-3-methyl-3,4-dihydroquinazolin-4-oneYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-bromo-2-nitrobenzoic acid (1 g, 4.1 mmol) and InCl3 (0.88 g, 4 mmol) in N-methylformamide (6 mL, 100 mmol) was stirred at reflux overnight (ca. 18 h). After it was cooled to room temperature, the mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the desired product (0.5 g). MS (ESI): 239 (MH+).

Workup

  1. temperatureat reflux overnight (ca. 18 h)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-4995976578c748af8416eee18ba5dcff
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…