Acetaldehyde → HCID 15462583, compound

HRID 376328Notes

Reaction equation

HRID 376328 reaction equation
[NH2:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[N:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3.[CH:24](=O)[CH3:25].[BH4-].[Na+].O>C(O)C>[CH2:24]([NH:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[N:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[CH3:25]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 18691101HCID 18691101, compound2×

Product 1

HCID 15462583HCID 15462583, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5 g of 3-amino-9-methoxy-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 26) in 100 ml of ethanol was added 3.0 ml of acetaldehyde, and the mixture was stirred at room temperature for 3 hours. After 3.3 g of sodium borohydride was added to the mixture and refluxed for 2 hours, the reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with saturated saline, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The crude crystal was recrystallized from petroleum ether/ethyl acetate to give 5 g of the title compound as colorless needles.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe crude crystal was recrystallized from petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-df76ea333494400fb922dba166419447
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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