Ethanethiol → 1-Ethylsulfanyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 1406176Notes

Reaction equation

HRID 1406176 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Cl)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:20]([SH:22])[CH3:21]>>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([S:22][CH2:20][CH3:21])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 6343EthanethiolHCID 860145021-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667132831-Ethylsulfanyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Conditions

Temperature
70 °C

Procedure

52 mg of 1-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester, Example D-20c, was dissolved in 2 ml of ethanethiol and heated in a sealed tube at 70° C. for 24 h, and 100° C. for 48 h. The resultant solution was concentrated under vacuum and the residue (54 mg) was purified by chromatography on silica gel using a gradient of 0 to 20 percent ethyl acetate in hexanes to elute the product. 25 mg of product was obtained; MS (+): m/z 306.06 (M+1)

Workup

  1. concentrationThe resultant solution was concentrated under vacuum
  2. customthe residue (54 mg) was purified by chromatography on silica gel using a gradient of 0 to 20 percent ethyl acetate in hexanes
  3. washto elute the product

Sources & evidence

ORD record
ord-acedd3b82545423eb13b9c38ac232f52
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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