6-bromo-7-methyl-8-nitroquinazolin-4(3H)-one → 8-amino-7-methylquinazolin-4(3H)-one

HRID 1042293Notes

Reaction equation

HRID 1042293 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:13]([O-])=O)[C:11]=1[CH3:12])[N:8]=[CH:7][NH:6][C:5]2=[O:16]>CCO>[NH2:13][C:10]1[C:11]([CH3:12])=[CH:2][CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][NH:6][C:5]2=[O:16]

Participants

3

Reactant 1

HCID 1358945796-bromo-7-methyl-8-nitroquinazolin-4(3H)-one

Product 1

HCID 1357422638-amino-7-methylquinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Bromo-7-methyl-8-nitroquinazolin-4(3H)-one (4.8 g, 17 mmol) was suspended in EtOH (500 ml) and degassed using a vacuum line. The mixture was then evacuated with nitrogen and 10% Pd/C (1.4 g) was added under a positive flow of nitrogen. The reaction was then placed under a hydrogen atmosphere with a large balloon while stirring. After 4 days, the reaction was filtered through a pad of celite. The filtrate was reduced under vacuum and the residue was triturated with ether to give 8-amino-7-methylquinazolin-4(3H)-one as an off white solid. MS Found: (ESI pos. ion) m/z 176 (M+H+).

Workup

  1. customdegassed
  2. customThe mixture was then evacuated with nitrogen and 10% Pd/C (1.4 g)
  3. additionwas added under a positive flow of nitrogen
  4. filtrationthe reaction was filtered through a pad of celite
  5. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-55b717dc38ab4a9198acf8b84d5c1a2c
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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