Hydrochloric Acid → 5-Chloroisoquinoline-4-carboxylic acid

HRID 1470505Notes

Reaction equation

HRID 1470505 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([O:14]C)=[O:13])=[CH:5][N:6]=[CH:7]2.[OH-].[K+].Cl>CO.O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([OH:14])=[O:13])=[CH:5][N:6]=[CH:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68281881Methyl 5-chloroisoquinolin-4-carboxylate

Product 1

HCID 682819645-Chloroisoquinoline-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of methyl 5-chloroisoquinolin-4-carboxylate (Intermediate-42) (3.8 g, 17.1 mmol) in MeOH (30 mL) was added, KOH (9.62 g, 171 mmol) solution in H2O (20 mL) and the reaction mixture was heated to 70° C. for 3 h. After completion (TLC), it was concentrated under vacuum to give crude product (3.5 g) that was diluted with water, acidified with 1N HCl (pH=3) and the aqueous phase was extracted with EtOAc, dried and concentrated under vacuum to afford the desired acid derivative (3 g, 84%) as an off white solid.

Workup

  1. concentrationAfter completion (TLC), it was concentrated under vacuum
  2. customto give crude product (3.5 g) that
  3. extractionthe aqueous phase was extracted with EtOAc
  4. customdried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1cecb7aa22be4b98b26767766448b1a9
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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