Dimethylformamide → 3-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine

HRID 251940Notes

Reaction equation

HRID 251940 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[C:8]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)=[N:9][CH:10]=[CH:11][CH:12]=1.[OH-].[Na+].CN(C)[CH:22]=[O:23]>>[Cl:6][C:7]1[C:8]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[CH:22]=[O:23])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 587620843-chloro-2-(1H-pyrrol-1-yl)pyridine

Product 1

HCID 587620783-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine

Procedure

To 3.8 ml of N,N-dimethylformamide was added dropwise 4.2 ml of phosphorus oxychloride at room temperature, and the mixture was stirred at room temperature for 30 minutes. Thereto 1.6 g of 3-chloro-2-(1H-pyrrol-1-yl)pyridine was added, and the resulting mixture was stirred at 60° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, and then slowly added to ice-water. The mixture was adjusted to pH 4 by an addition of a 2N aqueous sodium hydroxide solution. A deposited precipitate was collected by filtration to obtain 1.7 g of 3-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine of the formula:

Workup

  1. stirringthe resulting mixture was stirred at 60° C. for 2 hours
  2. temperatureto cool to room temperature
  3. filtrationA deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-d11fe155d1764685b0c7f31444247387
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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