Hexane → 2-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

HRID 1900745Notes

Reaction equation

HRID 1900745 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[CH:10][C:9]([CH3:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:16])[NH:7]2.[Br:17]N1C(=O)CCC1=O.CCCCCC>C(Cl)(Cl)Cl>[Br:17][CH2:14][CH:13]1[O:1][C:2]2=[C:3]3[C:8](=[C:9]([CH3:15])[CH:10]=[C:11]2[CH2:12]1)[NH:7][C:6](=[O:16])[CH:5]=[CH:4]3

Participants

5

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 233695765-Hydroxy-6-allyl-8-methylcarbostyril

Product 1

HCID 233696452-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-oneYield 103.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 5-hydroxy-8-methyl-6-(2-propenyl) carbostyril (64.57 g) in chloroform (2000 ml) was combined with N-bromosuccinimide (56.47 g) and refluxed with heat for 3 hours while stirring. The reaction mixture became yellow uniform solution. The reaction solution was washed with water, dried and condensed. n-Hexane was added to the concentrate, and crystallized. 91.40 g of the title compound was obtained as white powder.

Workup

  1. temperaturerefluxed
  2. temperaturewith heat for 3 hours
  3. washThe reaction solution was washed with water
  4. customdried
  5. customcondensed
  6. customcrystallized

Sources & evidence

ORD record
ord-f3634ecf41f648d4808c0c84e05e924a
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…