Cysteamine Hydrochloride → 2-[1-(2-Aminoethylthio)methyl]-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900750Notes

Reaction equation

HRID 1900750 reaction equation
Br[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.Cl.[NH2:19][CH2:20][CH2:21][SH:22].[OH-].[Na+]>CN(C)C=O.O>[NH2:19][CH2:20][CH2:21][S:22][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3

Participants

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 233696452-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 233695892-[1-(2-Aminoethylthio)methyl]-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (0.882 g) in dimethylformamide (40 ml), cysteamine hydrochloride (3.41 g) and caustic soda (2.40 g) in water (20 ml) were added and stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was combined with water, and extracted with chloroform. The extract was washed with water and dried. The solvent was evaporated and the residue was crystallized from chloroform--n-hexane to obtain 0.714 g of the title compound as pale yellow prisms (mp.: 182°-184° C.).

Workup

  1. additionwere added
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. customThe solvent was evaporated
  7. customthe residue was crystallized from chloroform

Sources & evidence

ORD record
ord-f3c1f2aa50194a9ab9fd6e281ccb1182
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…