Sodium Hydroxide → 1-Chloroisoquinoline-5-carboxylic acid--hydrogen chloride (1/1)

HRID 1067237Notes

Reaction equation

HRID 1067237 reaction equation
[C:1]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[C:11]2[Cl:16])([O:3]CC)=[O:2].[OH-].[Na+]>>[ClH:16].[C:1]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[C:11]2[Cl:16])([OH:3])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 21192504HCID 21192504, compound

Product 1

HCID 211924821-Chloroisoquinoline-5-carboxylic acid--hydrogen chloride (1/1)Yield 200%

Procedure

A solution of 5-carbethoxy-1-chloroisoquinoline (German Patent DE 2816863) (1.75 g, 7.4 mmol) and NaOH (0.8 g, 20 mmol) in MeOH-H20 (50 mL, 4:1) was stirred at 23° C. for 5 h. The solvents were evaporated in vacuo and the residue partioned between CH2Cl2 and aqueous NaOH (2 M). The aqueous phase was acidified with conc HCl and extracted with copious EtOAc (×4). The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo to leave 5-carboxy-1-chloroisoquinoline hydrochloride (1.8 g, 7.4 mmol) as a white solid.

Workup

  1. customThe solvents were evaporated in vacuo
  2. extractionextracted with copious EtOAc (×4)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c97053a8ffd4b808fad88578aa6842a
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

Loading…