Water → 1-Isoquinolinyloxyacetaldehyde dimethyl acetal

HRID 495425Notes

Reaction equation

HRID 495425 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6]O.Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1.[OH2:21]>CN(C=O)C>[CH3:9][O:8][C:5]([O:4][CH3:3])([O:21][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1)[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 140539Isoquinoline, 1-chloro-HCID 5423812,2-Dimethoxyethanol

Product 1

HCID 693569501-Isoquinolinyloxyacetaldehyde dimethyl acetalYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (60% oil dispersion, 1.2 g, 30 mmol) in DMF (6 mL) was added dropwise 2-hydroxyacetaldehyde dimethyl acetal (3.2 g, 30 mmol). The resulting mixture was left to stir for 0.5 h, then a solution of 1-chloroisoquinoline (1.6 g, 10 mmol) in DMF (2 mL) was added and the mixture was stirred at 80° C. for 24 h. The mixture was then poured into water (150 mL) and extracted with ether (2×150 mL). The combined organic extracts were dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane) to give 1-isoquinolinyloxyacetaldehyde dimethyl acetal (1.5 g, 64%).

Workup

  1. waitThe resulting mixture was left
  2. stirringthe mixture was stirred at 80° C. for 24 h
  3. extractionextracted with ether (2×150 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c53cdda6ad9d41d5bf99f29db8776956
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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