Sodium Hydroxide → 3,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acid

HRID 383757Notes

Reaction equation

HRID 383757 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:22])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>CO>[CH3:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:19])([F:20])[F:21])=[C:8]([CH3:22])[NH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 598075413,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 672524593,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acidYield 34.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acid ethyl ester (0.96 g) in methanol was added 4 N NaOH (6 mL). The reaction mixture was then heated to reflux with stirring overnight. After cooling, solvent was removed and the crude material was diluted with water. Solids were removed by filtration and washed with water. The aqueous filtrate was acidified with formic acid to precipitate the product. The precipitates were collected by filtration and washed with water, and then dried under high vacuum to afford 3,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acid (0.30 g). MS (ES): 284 (MH+). In a manner similar to that described in Example 16D, the title compound was prepared from 3,5-dimethyl-4-(2-trifluoromethyl-phenyl)-1H-pyrrole-2-carboxylic acid. 1H-NMR (CDCl3): δ 9.68 (1H, s), 7.89 (2H, m), 7.79 (3H, m), 7.73 (1H, s), 7.59 (1H, m), 7.50 (1H, M), 7.24 (1H, d), 3.05 (3H, s), 3.05 (3H, s), 2.19 (3H, s), 2.06 (3H, s); MS (ES): 437 (MH+).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customsolvent was removed
  5. additionthe crude material was diluted with water
  6. customSolids were removed by filtration
  7. washwashed with water
  8. customto precipitate the product
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with water
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-2eeaa08fe9ba4106997ba95ca16691b0
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

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