N-bromobutanimide → 9-bromomethyl-3-methylbenzo[f]quinazolin-1(2H)-one

HRID 1884028Notes

Reaction equation

HRID 1884028 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.[Br:18]N1C(=O)CCC1=O>C1C=CC=CC=1>[Br:18][CH2:17][C:14]1[CH:15]=[CH:16][C:7]2[CH:6]=[CH:5][C:4]3[N:3]=[C:2]([CH3:1])[NH:11][C:10](=[O:12])[C:9]=3[C:8]=2[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 135622202HCID 135622202, compound

Product 1

HCID 1354009769-bromomethyl-3-methylbenzo[f]quinazolin-1(2H)-oneYield 83%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a hot solution of 3,9-dimethylbenzo[f]quinazolin-1(2H)-one (4.00 g, 17.9 mmol) in benzene (2000 ml) under nitrogen was added N-bromo-succinimide (4.00 g, 22.5 mmol). The reaction mixture was stirred just below reflux for 30 minutes, then at a gentle reflux for 30 minutes. The resulting suspension was allowed to cool for 2 hours, the solid filtered and dried at 70° C. under reduced pressure to give 9-bromomethyl-3-methylbenzo[f]quinazolin-1(2H)-one (4.32 g, 83% purity by NMR). 1H NMR (DMSO-d6, 300 MHz) δ: 2.45 (s, 3H, CH3), 4.96 (s, 2H, CH2), 7.65 (d, J=9 Hz, 1H, Ar), 7.70 (dd, J=8, 2 Hz, 1H, Ar), 8.05 (d, J=8 Hz, 1H, Ar), 8.16 (d, J=9 Hz, 1H, Ar), 9.89 (s, 1H, Ar), 12.7 (br s, 1H, NH).

Workup

  1. temperaturebelow reflux for 30 minutes
  2. temperatureat a gentle reflux for 30 minutes
  3. temperatureto cool for 2 hours
  4. filtrationthe solid filtered
  5. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-b95402d4f9444752b6a4293d7fbddbfe
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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