Water → 1-(5-Acetylpyridin-2-yl)pyrrole-3-carboxylic acid

HRID 1748568Notes

Reaction equation

HRID 1748568 reaction equation
C([O:5][C:6]([C:8]1[CH:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][N:14]=2)[CH:9]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.O>ClCCl>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH:11]=[CH:12][C:8]([C:6]([OH:7])=[O:5])=[CH:9]2)=[N:14][CH:15]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 866925131-(5-Acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester

Product 1

HCID 866925141-(5-Acetylpyridin-2-yl)pyrrole-3-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester (380 mg) in dichloromethane (5 ml) were added trifluoroacetic acid (3 ml) and water (0.3 ml), and stirred at room temperature. After completion of the reaction, the solvent was evaporated in vacuo, to the residue was added water, 1 N aqueous solution of sodium hydroxide was added thereto under ice-cooling to adjust the mixture to pH 10, diethyl ether was added thereto, and the aqueous layer was separated. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling, the precipitated solid was collected by filtration, and dried at 60° C. under air blow to give the titled compound (300 mg) as a white solid. MS (ESI) m/z: 231

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated in vacuo, to the residue
  3. additionwas added water, 1 N aqueous solution of sodium hydroxide
  4. additionwas added
  5. temperatureunder ice-cooling
  6. additionwas added
  7. customthe aqueous layer was separated
  8. additionTo the aqueous layer was added concentrated hydrochloric acid under ice-
  9. temperaturecooling
  10. filtrationthe precipitated solid was collected by filtration
  11. customdried at 60° C. under air blow

Sources & evidence

ORD record
ord-2ce4b7f4e7ec49ac9187a126da7bdc7b
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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