Hydrochloric Acid → HCID 135773201, compound

HRID 904669Notes

Reaction equation

HRID 904669 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:7]2Cl)(=[O:3])[CH3:2].[S-:23][CH2:24][CH3:25].[Na+].C(S)C.[H-].[Na+].Cl>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:7]2[S:23][CH2:24][CH3:25])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 4459711Sodium ethanethiolateHCID 136035444HCID 136035444, compound

Product 1

HCID 135773201HCID 135773201, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-acetyl-4-chloro-7-hydroxy-8-propylquinoline-2-carboxylate (1.0 g) in dry dimethylformamide (50 mls) was added dropwise to a stirred solution of sodium thioethoxide [made by the addition of ethanethiol (0.773 g) to 50% sodium hydride in oil (0.6 g) in dry dimethylformamide (30 mls) under nitrogen]. The purple solution was stirred for 2 hours, poured into ethyl acetate and acidified with dilute hydrochloric acid. The organic layer was separated, washed with water, sodium bicarbonate solution and then dried. Evaporation of the solvent gave 0.8 g of the desired product which was recrystallised from cyclohexane to give 0.52 g of yellow needles mp 193°-195°.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, sodium bicarbonate solution
  3. customdried
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e7efb66e8fbf4190926ab09e7eb8049d
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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