Acetone → HCID 66854092, compound

HRID 251978Notes

Reaction equation

HRID 251978 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:21]=[O:22])[N:11]([C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[CH:15][C:14]=2[Cl:20])[CH:12]=1.CC(C)=[O:25].[OH-].[Na+]>O>[Br:7][C:8]1[CH:9]=[C:10]([C:21]([OH:25])=[O:22])[N:11]([C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[CH:15][C:14]=2[Cl:20])[CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 866325544-bromo-1-(3,5-dichloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 66854092HCID 66854092, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2.9 g of potassium permanganate in 15 ml of water was added dropwise to a mixture of 2.86 g of 4-bromo-1-(3,5-dichloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde and 30 ml of acetone while the mixture was maintained at 40° C. The mixture was stirred at 40° C. for 2 hours. A precipitate was filtered off to obtain a filtrate. The filtrate was adjusted to pH 10-12 by an addition of a 2N aqueous sodium hydroxide solution, and then washed with chloroform two times. The aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid. A deposited precipitate was collected by filtration to obtain 2.08 g of 4-bromo-1-(3,5-dichloro-4-pyridinyl)-1H-pyrrole-2-carboxylic acid of the formula:

Workup

  1. filtrationA precipitate was filtered off
  2. customto obtain a filtrate
  3. washwashed with chloroform two times
  4. additionThe aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid
  5. filtrationA deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-5c0276b26e3f4f5483d1a68191f99a25
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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