Pyridine → 9-bromo-3-methylbenzo[f]quinazolin-1(2H)-one

HRID 1377046Notes

Reaction equation

HRID 1377046 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:14][CH2:13][C:12]3[N:11]=[C:10]([CH3:15])[NH:9][C:8](=[O:16])[C:7]=3[C:6]=2[CH:17]=1.BrN1C(=O)CCC1=O.N1C=CC=CC=1.NC1NC(=O)C2C3C=C(Br)C=CC=3C=CC=2N=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:14]=[CH:13][C:12]3[N:11]=[C:10]([CH3:15])[NH:9][C:8](=[O:16])[C:7]=3[C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 67184N-bromobutanimideHCID 1354229133-Amino-9-bromobenzo[f]quinazolin-1(2H)-oneHCID 1358381179-Bromo-5,6-dihydro-3-methylbenzo[f]quinazolin-1(2H)-one

Product 1

HCID 1358381559-bromo-3-methylbenzo[f]quinazolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 9-Bromo-5,6-dihydro-3-methylbenzo[f]quinazolin-1(2H)-one (1.0 g, 3.4 mmoles), N-bromosuccinimide (0.63 g, 3.5 mmoles) and pyridine (0.3 ml, 3.7 mmoles) in dry benzene (350 ml) was reacted in the same manner as for the corresponding 3-pivalamide (Example 2). After cooling, benzene and excess pyridine were removed under reduced pressure. The residue was triturated with methanol:water (1:1) and filtered to leave a crude product which was recrystallized from methanol to give 9-bromo-3-methylbenzo[f]quinazolin-1(2H)-one as an off-white solid. (0.47 g, 37%) 1H NMR (DMSO-d6, 200 MHz) δ: 2.57(s, 3H, CH3); 7.73(d, J=9.0 Hz, 1H, Ar); 7.86(dd, J=8.6, 2.0 Hz, 1H, Ar); 8.09(d, J=8.7 Hz, 1H, Ar); 8.41(d, J=8.8 Hz, 1H, Ar); 9.92(d, J=2.0 Hz, 1H, Ar).

Workup

  1. temperatureAfter cooling
  2. custombenzene and excess pyridine were removed under reduced pressure
  3. customThe residue was triturated with methanol:water (1:1)
  4. filtrationfiltered
  5. customto leave a crude product which
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-37ca6ed6fdab453c9d33d42ed5aae42f
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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