Sodium Hydroxide → 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylic acid

HRID 1894712Notes

Reaction equation

HRID 1894712 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:10]([O:12]C)=[O:11])[NH:8][CH:9]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([C:10]([OH:12])=[O:11])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66646695methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 666469894-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylic acidYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a methanol 30 mL solution of methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate (840 mg, 3.1 mmol) was added 5N sodium hydroxide solution (3.1 mL, 16 mmol) and the reaction was stirred in an oil bath at 70° C. overnight. After cooling to rt, pH of the reaction mixture was adjusted to 1.5 to give a gray suspension. The precipitate was collected by suction filtration and dried under vacuum to give the title compound (796 mg).

Workup

  1. temperatureAfter cooling to rt
  2. customto give a gray suspension
  3. filtrationThe precipitate was collected by suction filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8b8ad8d6fd5542d8a313f0686c71b1af
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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