Pyridine → N-(9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide

HRID 1654343Notes

Reaction equation

HRID 1654343 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]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[NH:9][C:8](=[O:22])[C:7]=3[C:6]=2[CH:23]=1.N1C=CC=CC=1.BrN1C(=O)CCC1=O>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]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:18])[CH3:19])[NH:9][C:8](=[O:22])[C:7]=3[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67184N-bromobutanimideHCID 135838098N-(9-bromo-1,2,5,6-tetrahydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide

Product 1

HCID 135838104N-(9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N-(9-bromo-1,2,5,6-tetrahydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (1.09 g, 2.9 mmoles) and pyridine (0.28 ml, 3.5 mmoles) in dry benzene (100 ml) was stirred and heated to reflux under a nitrogen atmosphere. N-Bromosuccinimide (0.57 g, 3.2 mmoles) was added in a single portion, and the mixture was vigorously stirred and refluxed for 1.5 hours. After cooling, benzene and excess pyridine were removed under reduced pressure, leaving a light yellow residue which was then triturated with methanol:methylene chloride (1:1), filtered and dried to give N-(9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide. (0.4 g, 37%) 1H NMR(DMSO-d6, 200 MHz) δ: 1.26(s, 9H, t-butyl); 7.58(d, J=9.0 Hz, 1H, Ar); 7.74(dd, J=8.7, 2.1 Hz, 1H, Ar); 7.98(d, J=8.8 Hz, 1H, Ar); 8.25(d, J=9.0 Hz, 1H, Ar); 9.92(d, J=2.0 Hz, 1H, Ar); 11.35(br s, 1H, NH); 12.35(br s, 1H, NH).

Workup

  1. temperatureheated
  2. temperatureto reflux under a nitrogen atmosphere
  3. stirringthe mixture was vigorously stirred
  4. temperaturerefluxed for 1.5 hours
  5. temperatureAfter cooling
  6. custombenzene and excess pyridine were removed under reduced pressure
  7. customleaving a light yellow residue which
  8. customwas then triturated with methanol:methylene chloride (1:1)
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-2489787886354ef9aca7f53a3081607d
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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