Ethanol → Isoquinoline-4-carboxylic acid

HRID 1470480Notes

Reaction equation

HRID 1470480 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)C(C#N)=[CH:3][N:2]=1.[OH-:13].[K+].[CH3:15][CH2:16][OH:17]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:15]([C:16]([OH:13])=[O:17])=[CH:3][N:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 964504-Isoquinolinecarbonitrile

Product 1

HCID 459768Isoquinoline-4-carboxylic acidYield 59.3%

Procedure

To a stirred solution of isoquinolin-4-carbonitrile (Intermediate-13) (3.0 g, 19.45 mmol) in EtOH (30 mL) was added KOH (20 g in 20 mL water) and the mixture was refluxed overnight. It was then cooled to RT and concentrated under reduced pressure. The aqueous layer was washed with Et2O and neutralized using 1N HCl. It was extracted with EtOAc and the organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound (2 g, 59.3%) as an off white solid.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. concentrationconcentrated under reduced pressure
  3. washThe aqueous layer was washed with Et2O
  4. extractionIt was extracted with EtOAc
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2757b3d97688404c9d6261c1f43178d4
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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