Hydrochloric Acid → 1-Chloro-4-hydroxyisoquinoline-3-carboxylic acid

HRID 250304Notes

Reaction equation

HRID 250304 reaction equation
C([O:5][C:6]([C:8]1[N:9]=[C:10]([Cl:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[OH-].[Na+].O.Cl>C(O)C>[Cl:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([OH:7])=[O:5])[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 860145021-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 110205201-Chloro-4-hydroxyisoquinoline-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.23 g of 1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (33 mmol), 90 ml of 2.5N aqueous sodium hydroxide solution, water (20 ml) and ethanol (110 ml) was refluxed with stirring for 2 h. Then the pH of the mixture was adjusted to 2 by the addition of concentrated aqueous hydrochloric acid. During the addition, the temperature of the mixture was kept at 20° C. by cooling with an ice bath. Stirring was then continued for 1 h before the solid component was separated by vacuum filtration. The filter cake was washed with water and dried in vacuo at 85° C. to give a white powder. 6.64 g of the title compound were obtained; MS-(+)-ion: M+1=224.1 amu.

Workup

  1. temperaturewas refluxed
  2. additionDuring the addition
  3. customwas kept at 20° C.
  4. temperatureby cooling with an ice bath
  5. stirringStirring
  6. waitwas then continued for 1 h before the solid component
  7. customwas separated by vacuum filtration
  8. washThe filter cake was washed with water
  9. customdried in vacuo at 85° C.
  10. customto give a white powder

Sources & evidence

ORD record
ord-ed749d4451a34ef3a19bf507d693f7ce
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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