Sodium Hydroxide → 2-[2-(Dimethylamino)ethylthiomethyl]-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900749

Reaction equation

HRID 1900749 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.[CH3:18][N:19]([CH2:21][CH2:22][SH:23])[CH3:20].[OH-].[Na+]>CN(C)C=O.Cl.O>[CH3:18][N:19]([CH3:20])[CH2:21][CH2:22][S:23][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

7

Reactant 3

HCID 14798Sodium HydroxideHCID 25799CaptamineHCID 233696452-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 233696732-[2-(Dimethylamino)ethylthiomethyl]-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneYield 91.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (1. 765 g) in dimethylformamide (60 ml), hydrochloric acid salt of 2 (dimethylamino)ethylmercaptan (4.25 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 NaCl solution twice and dried and condensed. The residue was crystallized from chloroform--n-hexane to obtain 1.741 g of the title compound as white powder (mp.: 163°-165° C.).

Workup

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

Sources & evidence

ORD record
ord-9c5b9c9f1a514ec1a9a9042f54391201
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Linked notes

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