Dimethylformamide → 1-(2-nitrophenyl)-1H-pyrrole-2-carbaldehyde

HRID 1739955Notes

Reaction equation

HRID 1739955 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:24]=[O:25]>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:24]=[O:25])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 5206111-(2-Nitrophenyl)pyrrole

Product 1

HCID 47153911-(2-nitrophenyl)-1H-pyrrole-2-carbaldehyde

Conditions

Temperature
90 °C

Procedure

To a solution of 3.76 g of 1-(2-nitrophenyl)pyrrole in 20 ml of N,N-dimethylformamide at 0° C. is added dropwise with stirring 3 ml of phosphorus oxychloride. Stirring is continued for 30 minutes and the reaction mixture is heated at 90° C. for 1 hour. After cooling to room temperature the mixture is treated with crushed ice and the pH adjusted to 12 with 2N sodium hydroxide. The resulting suspension is filtered, washed-with water and dried to give 5.81 g of the desired product as a light yellow solid m.p. 119°-122° C.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. additionis treated with crushed ice
  3. filtrationThe resulting suspension is filtered, washed-with water
  4. customdried

Sources & evidence

ORD record
ord-095b02444c7b45818e0e4803f783a464
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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