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

HRID 1788929Notes

Reaction equation

HRID 1788929 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
80 °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. temperaturecooled
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-cb697b53c8a94fa7a4450949dd32dd23
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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