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

HRID 556730

Reaction equation

HRID 556730 reaction equation
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)([O-:13])=[O:12].CC([O-])=O.[Na+]>C(Cl)(Cl)(Cl)Cl.O>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:9]=[O:10])([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 5206111-(2-Nitrophenyl)pyrrole

Product 1

HCID 47153911-(2-nitrophenyl)-1H-pyrrole-2-carbaldehydeYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

POCl3 was added to DMF at 0-10° C. after which 50 ml of CCl4 was added at room temperature. A solution of 4.5 g (24 mmol) 1a in 50 ml of CCl4 was added slowly to the reaction mixture at about 10° C. during 1 hour. The reaction mixture was refluxed for 15 min. and a solution of 50 g of NaOAc, 3H2O in 50 ml of H2O was added and refluxing was continued for 15 min. The mixture was cooled, extracted with ether and dried over Na2SO4. 8.0 g (65%) of 2a was isolated by column chromatography using EtOAc:petroleum ether as eluent.

Workup

  1. additionwas added at room temperature
  2. temperatureThe reaction mixture was refluxed for 15 min.
  3. temperaturerefluxing
  4. temperatureThe mixture was cooled
  5. extractionextracted with ether
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e51942fef4734edd9a97c030c059bd16
Source dataset
uspto-grants-2011_11
Patent number
US08058306B2

Linked notes

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