Acetone → 4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid

HRID 2427052Notes

Reaction equation

HRID 2427052 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:20]=[O:21])[N:11]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:12]=1.CC(C)=[O:24].[OH-].[Na+]>O>[Br:7][C:8]1[CH:9]=[C:10]([C:20]([OH:24])=[O:21])[N:11]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 866325474-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 668544874-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

An aqueous solution of 1.2 g of potassium permanganate in 10 ml of water was added dropwise to a mixture of 0.72 g of 4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehyde and 15 ml of acetone while the mixture was retained at 40° C. The mixture was then stirred at 60° C. for 8 hours. Precipitates were 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 0.56 g of 4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid of the formula:

Workup

  1. customwas retained at 40° C
  2. customPrecipitates
  3. filtrationwere filtered off
  4. customto obtain a filtrate
  5. washwashed with chloroform two times
  6. additionThe aqueous layer was adjusted to around pH 3 by an addition of 2N hydrochloric acid
  7. filtrationA deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-58dd30f12aa54ec78fe245e8d7e26051
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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