N-bromobutanimide → 6-(Bromomethyl)-1-methylquinolin-2(1H)-one

HRID 1682543Notes

Reaction equation

HRID 1682543 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[O:13].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:14][CH2:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[C:3](=[O:13])[CH:4]=[CH:5]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1216042(1H)-Quinolinone, 1,6-dimethyl-

Product 1

HCID 151990656-(Bromomethyl)-1-methylquinolin-2(1H)-oneYield 33%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 28b (22 g, 0.127 mol) and N-bromosuccinimide (23 g, 0.13 mol) in CCl4 (400 mls) was irradiated for 2.5 hours with a 275 watt heat lamp after an addition of AIBN (50 mg) to initiate the free radical reaction. During this time, the reaction achieved reflux. After cooling, the mixture was concentrated to a small volume and ethyl acetate (400 mls) and water (150 mls) were added and the layers separated. The organic phase was dried (MgSO4) and evaporated. The crude material was purified by chromatography on silica gel using 35% ethyl acetate/toluene to give the product 28c (10.4 g, 33%) as a solid, mp 99°-100° C. The structural assignment was supported by the 1H-NMR spectrum. Analysis calculated for C11H10NOBr: C, 52.41; H, 4.00; N, 5.56; Br, 31.69. Found: C, 52.11; H, 3.91; N, 5.40; Br, 31.40.

Workup

  1. temperatureheat lamp
  2. customthe free radical reaction
  3. temperatureDuring this time, the reaction achieved reflux
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated to a small volume and ethyl acetate (400 mls) and water (150 mls)
  6. additionwere added
  7. customthe layers separated
  8. dry with materialThe organic phase was dried (MgSO4)
  9. customevaporated
  10. customThe crude material was purified by chromatography on silica gel using 35% ethyl acetate/toluene

Sources & evidence

ORD record
ord-c8e0b1e30d7b45ac9e55e227d25b5f8d
Source dataset
uspto-grants-1997_06
Patent number
US05635514

Reaction notes

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