Sodium Hydroxide → [5-(4-Chlorobenzoyl)-4-methoxy-1-methyl-1H-pyrrol-2-yl]acetic acid

HRID 1388922Notes

Reaction equation

HRID 1388922 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][C:6]1[N:7]([CH3:22])[C:8]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:9]([O:11][CH3:12])[CH:10]=1)C.[OH-].[Na+]>C(O)C.O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]([C:8]2[N:7]([CH3:22])[C:6]([CH2:5][C:4]([OH:23])=[O:3])=[CH:10][C:9]=2[O:11][CH3:12])=[O:21])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20469123Ethyl-5-(p-chlorobenzoyl)-4-methoxy-1-methylpyrrole-2-acetate

Product 1

HCID 13345722[5-(4-Chlorobenzoyl)-4-methoxy-1-methyl-1H-pyrrol-2-yl]acetic acidYield 88.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl-5-(p-chlorobenzoyl)-4-methoxy-1-methylpyrrole-2-acetate (145 mg, 0.475 mmole) is dissolved in 1 ml hot ethanol under nitrogen. Subsequently, 2 ml of 2.5 N aqueous sodium hydroxide is added dropwise. The solution is heated at 95° for about 5 min. The reaction solution is then diluted with water, the product precipitated with 2.5 ml of 2.5 N hydrochloric acid. The resulting precipitate is filtered, washed with water and dried in vacuo to yield 130 mg of 5-(p-chlorobenzoyl)-4-methoxy-1-methylpyrrole-2-acetic acid, m.p. 148 (dec).

Workup

  1. temperatureThe solution is heated at 95° for about 5 min
  2. customthe product precipitated with 2.5 ml of 2.5 N hydrochloric acid
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-fd8e486c341f400a850ccd3cbcebc93a
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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