Methyl 3-isoquinolinecarboxylate → Isoquinoline-3-carboxaldehyde

HRID 742504

Reaction equation

HRID 742504 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:5]([CH:3]=[O:2])[N:6]=1

Participants

4

Reactant 2

HCID 725374Methyl 3-isoquinolinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 231555Isoquinoline-3-carboxaldehydeYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Isoquinolinecarboxaldehyde (7 g, 84%) was prepared by reduction of 3-isoquinolinecarboxylic acid methyl ester (10 g, 52 mmol) with 1M LAH (27 ml in THF, 27 mmol) in 300 ml of dry THF at -78° C. for 30 minutes. The mixture was quenched with 7 ml of acetic acid, concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate, 2:1) to afford 7 g (84%) of 3-iso-quinolinecarboxaldehyde.

Workup

  1. customThe mixture was quenched with 7 ml of acetic acid
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-5523d22bbb1c43b4bc07ab65d3251fe7
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Linked notes

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