N-bromobutanimide → 2-Bromomethyl-5,8-dimethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

HRID 1900810Notes

Reaction equation

HRID 1900810 reaction equation
[CH2:1]([C:4]1[C:5]([OH:17])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[NH:10][C:9](=[O:15])[C:8]([CH3:16])=[CH:7]2)[CH:2]=[CH2:3].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:18][CH2:3][CH:2]1[O:17][C:5]2=[C:6]3[C:11](=[C:12]([CH3:14])[CH:13]=[C:4]2[CH2:1]1)[NH:10][C:9](=[O:15])[C:8]([CH3:16])=[CH:7]3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 233696046-Allyl-5-hydroxy-3,8-dimethylcarbostyril

Product 1

HCID 233695562-Bromomethyl-5,8-dimethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-oneYield 65.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
75 °C

Procedure

To 6-allyl-5-hydroxy-3,8-dimethylcarbostyril (3.86 g, 16.68 mmol), N-bromsuccinimide (3.0 g, 16.68 mmol) and chloroform (140 ml) were added, and stirred for 25 minutes in a bath at 75° C. After cooling, the mixture was washed with water, dried, and condensed. The resultant residue was subjected to recrystallization (chloroform-methanol-ether) to obtain 3.36 g of the title compound as pale yellow prisms (64.7%).

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with water
  3. customdried
  4. customcondensed
  5. customThe resultant residue was subjected to recrystallization (chloroform-methanol-ether)

Sources & evidence

ORD record
ord-ce70171f5439451085d25d294803dff1
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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