Dimethylformamide → 7-Chloro-3-formyl-2methylimidazo[2,1-a]isoquinoline

HRID 649154Notes

Reaction equation

HRID 649154 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:7]12.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:25]=[O:26]>>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[C:14]([CH:25]=[O:26])=[C:13]([CH3:15])[N:12]=[C:7]12

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 138218267-Chloro-2-methylimidazo[2,1-a]isoquinoline

Product 1

HCID 138218487-Chloro-3-formyl-2methylimidazo[2,1-a]isoquinoline

Conditions

Temperature
87.5 °C

Procedure

A solution of 7-chloro-2-methylimidazo[2,1-a]isoquinoline (4 g) in N,N-dimethylformamide (40 ml) was added dropwise to a mixture of N,N-dimethylformamide (5.7 ml) and phosphoryl chloride (1.86 ml) under ice cooling. After being stirred at 85-90° C. for 6 hours, the mixture was poured into ice-water, basified with aqueous sodium hydroxide, heated at 80° C. for 20 minutes and cooled. The resulting precipitate was collected by filtration, washed with water and recrystallized from methanol to give 7-chloro-3-formyl-2methylimidazo[2,1-a]isoquinoline (0.356 g).

Workup

  1. temperatureheated at 80° C. for 20 minutes
  2. temperaturecooled
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c150e2bdce4a4a61b8e9538d6edad932
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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