Sodium Hydroxide → HCID 10016371, compound

HRID 863630Notes

Reaction equation

HRID 863630 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][C:6]1[N:7]([CH3:20])[C:8]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)C.[OH-].[Na+]>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([C:8]2[N:7]([CH3:20])[C:6]([CH2:5][C:4]([OH:21])=[O:3])=[CH:10][CH:9]=2)=[O:19])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 18424207HCID 18424207, compound

Product 1

HCID 10016371HCID 10016371, compound

Procedure

A suspension of 3.06 g. (0.01 mole) of ethyl-5-(ρ-chlorobenzoyl)-1-methylpyrrole-2-acetate in 25 ml. of 0.5N sodium hydroxide is refluxed for 30 minutes. About two-thirds of this solution is cooled, washed with ether, and then acidified with dilute hydrochloric acid. The resulting solid precipitate is collected by filtration, dried and recrystallized from ethanol-water to give the product, 5-(ρ-chlorobenzoyl)-1-methylpyrrole-2-acetic acid; M.P. 189°-191° C. Upon recrystallization from ethanol-water, the melting point is 188°-190° C. The other one-third of the solution is cooled in an ice-bath whereupon the yellow sodium salt of the acid is precipitated and collected by filtration.

Workup

  1. additionA suspension of 3.06 g
  2. temperatureAbout two-thirds of this solution is cooled
  3. washwashed with ether
  4. filtrationThe resulting solid precipitate is collected by filtration
  5. customdried
  6. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-7ba0d78e975440218d923eda66fe827d
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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