Acetone → HCID 86632557, compound

HRID 251985Notes

Reaction equation

HRID 251985 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:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=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:14]([Cl:19])=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 86632556HCID 86632556, compound

Product 1

HCID 86632557HCID 86632557, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4.43 g of potassium permanganate in 15 ml of water was added dropwise to a mixture of 4.22 g of 4-bromo-1-(2-chloro-3-pyridinyl)-1H-pyrrole-2-carbaldehyde and 30 ml of acetone while the mixture was maintained at 40° C. The resulting 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, and then extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3.02 g of 4-bromo-1-(2-chloro-3-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. extractionextracted with ethyl acetate two times
  6. washwashed successively with water
  7. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-976bf25d15374224b12fcde4a0411725
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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