Acetic Anhydride → 3-Acetoxymethyl-7-chloro-2-methylimidazo[2,1-a]isoquinoline

HRID 1788938Notes

Reaction equation

HRID 1788938 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[Cl:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]1[C:21](CO)=[C:20](C)[N:19]=[C:14]12>N1C=CC=CC=1>[C:5]([O:4][CH2:1][C:2]1[N:13]2[CH:12]=[CH:11][C:10]3[C:15]([C:14]2=[N:19][C:20]=1[CH3:21])=[CH:16][CH:17]=[CH:18][C:9]=3[Cl:8])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 138218607-Chloro-3-hydroxymethyl-2-methylimidazo[2,1-a]isoquinoline

Product 1

HCID 138218613-Acetoxymethyl-7-chloro-2-methylimidazo[2,1-a]isoquinolineYield 35.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.71 g) was added dropwise to a suspension of 7-chloro-3-hydroxymethyl-2-methylimidazo[2,1-a]isoquinoline (1.43 g) in pyridine (14 ml) and the mixture was stirred at room temperature for 24 hours. The mixture was evaporated in vacuo and the residue was extracted with chloroform after an addition of water to it. The extract was washed with water, dried over magnesium sulfate, treated with activated charcoal and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 3-acetoxymethyl-7-chloro-2-methylimidazo[2,1-a]isoquinoline (0.6 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. extractionthe residue was extracted with chloroform
  3. additionafter an addition of water to it
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. customevaporated in vacuo
  8. customThe crystalline residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-1dc58f9bdebb49a9ac8f93e49b2889db
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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