Diisobutylaluminum hydride → Isoquinoline-3-carboxaldehyde

HRID 2220706Notes

Reaction equation

HRID 2220706 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5].CC(C[AlH]CC(C)C)C>O1CCCC1.CCCCCCC>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:6]([CH:4]=[O:5])[N:7]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 53404828HCID 53404828, compound

Product 1

HCID 231555Isoquinoline-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 1.35 g (6.24 mmol) of isoquinoline-3-carboxylic acid methoxy-methyl-amide was dissolved in 50 ml tetrahydrofuran, 7.49 mL of 1.0 M DIBAL solution in heptane was added at −78° C. The reaction was warmed to room temperature and stirred for 1 hour at r.t., and then quenched by addition of 10 mL saturated sodium bicarbonate. 100 mL of water was added followed by extraction with 100 ml of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuum to give colorless oil. The crude was used to next step without further purification. LC-MSD, m/z for C10H7NO [M+H]+: 158.2. LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 min: 0.221 min.

Workup

  1. customquenched by addition of 10 mL saturated sodium bicarbonate
  2. addition100 mL of water was added
  3. extractionfollowed by extraction with 100 ml of dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated in vacuum
  6. customto give colorless oil
  7. customThe crude was used to next step without further purification
  8. waitLC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 min
  9. custom0.221 min.

Sources & evidence

ORD record
ord-523983266bcf482a891193d00c3ea09d
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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