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

HRID 1419963Notes

Reaction equation

HRID 1419963 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
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1e35a6cd98f74e589d2011eccb3f6a9f
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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