Methyl 3-isoquinolinecarboxylate → Isoquinoline-3-carboxaldehyde

HRID 2099760Notes

Reaction equation

HRID 2099760 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11](OC)=[O:12])[N:2]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[O:12])[N:2]=1

Participants

4

Reactant 2

HCID 725374Methyl 3-isoquinolinecarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 231555Isoquinoline-3-carboxaldehydeYield 65.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 3-isoquinolinecarboxylate (2.0 g, 10.7 mmol) in toluene was cooled to −78° C. To the solution was added diisobutylaluminum hydride (1M in toluene, 21.4 mL, 21.4 mmol) slowly over 15 minutes via syringe. While still at −78° C., the reaction was quenched with a solution of ether (80 mL), acetic acid (20 mL) and water (8 mL) and then the mixture was allowed to slowly warm to room temperature overnight. The organics were decanted and the solvent was evaporated. Flash column chromatography (gradient 1:4 ethyl acetate/hexanes to 1:3 ethyl acetate/hexanes) provided 1.1 grams of the title compound (65% yield). 1H-NMR (CDCl3, 300 MHz) δ 10.24 (s, 1H), 9.35 (s, 1H), 8.36 (s, 1H), 8.07-7.98 (m, 2H), 7.82-7.32 (m, 2H). Mass spec.: 158 (MH)+.

Workup

  1. customWhile still at −78° C., the reaction was quenched with a solution of ether (80 mL), acetic acid (20 mL) and water (8 mL)
  2. customThe organics were decanted
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-30f92189eb5a4567b2421fded6e1152b
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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