Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate → Tolmetin

HRID 848045Notes

Reaction equation

HRID 848045 reaction equation
C([C:3]([OH:22])([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:4]1[N:8]([CH3:9])[C:7]([CH2:10][C:11]([O:13]C)=[O:12])=[CH:6][CH:5]=1)#N>[OH-].[Na+]>[CH3:9][N:8]1[C:4]([C:3](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:5][CH:6]=[C:7]1[CH2:10][C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 12940095Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate

Product 1

HCID 5509Tolmetin

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate, 55 mg (0.185 mmole) was heated on a steam bath in 15 percent NaOH (1.5 ml) for 3.5 hours. The reaction was cooled on ice for one hour then filtered. The solid was dissolved in distilled water, hot filtered, cooled, 3 N HCl was added to precipitate 0.48 g (100 percent) of 1-methyl-5-(4-methylbenzoyl)pyrrole-2-acetic acid, mp 153°-158°, undepressed by admixture with authentic material.

Workup

  1. temperatureThe reaction was cooled on ice for one hour
  2. filtrationthen filtered
  3. dissolutionThe solid was dissolved in distilled water
  4. temperaturehot filtered, cooled
  5. addition3 N HCl was added to precipitate 0.48 g (100 percent) of 1-methyl-5-(4-methylbenzoyl)pyrrole-2-acetic acid, mp 153°-158°

Sources & evidence

ORD record
ord-061692dab1d74a368cf808cb8a291c2c
Source dataset
uspto-grants-1981_10
Patent number
US04294760

Reaction notes

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