Ethyl Acetate → 7-Chloro-3-hydroxymethyl-2-methylimidazo[2,1-a]isoquinoline

HRID 649164Notes

Reaction equation

HRID 649164 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]1[C:20]([C:21](OCC)=[O:22])=[C:19]([CH3:26])[N:18]=[C:13]12.C(OCC)(=O)C>O1CCCC1>[Cl:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]1[C:20]([CH2:21][OH:22])=[C:19]([CH3:26])[N:18]=[C:13]12

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 138218627-Chloro-3-ethoxycarbonyl-2-methylimidazo[2,1-a]isoquinolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 138218607-Chloro-3-hydroxymethyl-2-methylimidazo[2,1-a]isoquinolineYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.668 g) was added portionwise to a solution of 7-chloro-3-ethoxycarbonyl-2-methylimidazo[2,1-a]isoquinoline (5.1 g) in tetrahydrofuran (100 ml) with ice-cooling under nitrogen atmosphere and the mixture was stirred at room temperature for 1.5 hours. After an addition of ethyl acetate, the mixture was evaporated in vacuo and the residue was extracted with hot ethanol. The extract was treated with activated charcoal and evaporated in vacuo. The residue was recrystallized from 90% ethanol to give 7-chloro-3-hydroxymethyl-2-methylimidazo[2,1-a]isoquinoline (1.94 g).

Workup

  1. temperaturecooling under nitrogen atmosphere
  2. customthe mixture was evaporated in vacuo
  3. extractionthe residue was extracted with hot ethanol
  4. additionThe extract was treated with activated charcoal
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from 90% ethanol

Sources & evidence

ORD record
ord-cef9f94a53654b7f922cc611c8e2b1ea
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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