Methanol → Methyl 3-chloroisoquinoline-8-carboxylate

HRID 920253Notes

Reaction equation

HRID 920253 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([OH:14])=[O:13].S(Cl)(Cl)=O.[CH3:19]O>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([O:14][CH3:19])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 895248833-Chloroisoquinoline-8-carboxylic acid

Product 1

HCID 89524931Methyl 3-chloroisoquinoline-8-carboxylate

Conditions

Temperature
65 °C

Procedure

A 20 mL microwave vial was charged with 3-chloroisoquinoline-8-carboxylic acid (1 g, 4.82 mmol) in 5 mL of MeOH and then was added with thionyl chloride (0.703 mL, 9.63 mmol). Stirred at 65° C. overnight and then concentrated in vacuo. Purified by silica gel chromatography (0-50% EtOAc in hexane) yielded Methyl 3-chloroisoquinoline-8-carboxylate (27-1).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurified by silica gel chromatography (0-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-78db16cbef6245fd9c63740650ea06cc
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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