Methyl isoquinoline-1-carboxylate → Isoquinoline-1-carbaldehyde

HRID 742494Notes

Reaction equation

HRID 742494 reaction equation
C[O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:5]1([CH:3]=[O:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 21196988Methyl isoquinoline-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 265306Isoquinoline-1-carbaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Isoquinolinecarboxaldehyde (7.3 g, 64%) was prepared from 1-isoquinolinecarboxylic acid methyl ester (13.6 g, 0.073 mol) and 1M LAH (36.6 ml in THF) in 300 ml of dry THF (J. Org. Chem., vol 28, p 1898, 1963) to afford 7.3 g (64%) of 1-isoquinolinecarboxaldehyde.

Sources & evidence

ORD record
ord-6f8825c6e5394f318dd8c9ce8b2ac8d9
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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