Tetrahydrofuran → Isoquinoline-3-carboxaldehyde

HRID 2220717Notes

Reaction equation

HRID 2220717 reaction equation
O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.CON(C)[C:19]([C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20]>CCCCCCC>[CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[C:21]([CH:19]=[O:20])[N:22]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 53404828HCID 53404828, compound

Product 1

HCID 231555Isoquinoline-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
-78 °C

Procedure

In 5 mL dry tetrahydrofuran 0.11 g (0.52 mmol) of isoquinoline-3-carboxylic acid methoxy-methyl-amide was dissolved, and cooled down to −78° C. under the atmosphere of nitrogen. 0.57 mL of 1M diisobutylaluminum hydride solution in heptane was added slowly. After the addition was complete, the solution was allowed to warm up to 0° C. over 2 hours and was quenched with ethyl acetate, and water was added, and extracted with dichloromethane. The organic solution was dried with anhydrous magnesium sulfate and evaporated in vacuum to give 60 mg of the crude aldehyde, which was used in the following steps without purification. LC-MSD, m/z for C10H7NO [M+H]+: 158.3.

Workup

  1. additionAfter the addition
  2. temperatureto warm up to 0° C. over 2 hours
  3. customwas quenched with ethyl acetate, and water
  4. additionwas added
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic solution was dried with anhydrous magnesium sulfate
  7. customevaporated in vacuum

Sources & evidence

ORD record
ord-2b8c3e5c6abe4aaeb29492b303bac8d4
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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