Sodium Hydroxide → 5-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid

HRID 1388920Notes

Reaction equation

HRID 1388920 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17]CC)=[O:16])=[C:10]([C:20]([O:22]CC)=[O:21])[C:9]=2[O:25][CH3:26])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=[O:16])=[C:10]([C:20]([OH:22])=[O:21])[C:9]=2[O:25][CH3:26])=[O:7])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20469108Ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate

Product 1

HCID 204691265-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acidYield 109.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate (505 mg) is suspended in 1 ml ethanol and heated to reflux. After all the solids dissolve, 5 ml of 2.5 N aqueous sodium hydroxide is added dropwise, causing an oil to separate at the end of the addition. However, the reaction mixture becomes homogeneous again after stirring vigorously at 100° for about 5 min. The reaction is then cooled, diluted with 5 ml water and acidified with 5.5 ml 2.5 N hydrochloric acid. The resulting precipitate is filtered, dried in vacuo to afford 478 mg of crude 5-(p-chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid.

Workup

  1. temperatureheated to reflux
  2. dissolutionAfter all the solids dissolve
  3. customto separate at the end of the addition
  4. temperatureThe reaction is then cooled
  5. additiondiluted with 5 ml water
  6. filtrationThe resulting precipitate is filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3e068ccef05d4ed2ad7b562226dc3999
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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