5-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid → [5-(4-Chlorobenzoyl)-4-methoxy-1-methyl-1H-pyrrol-2-yl]acetic acid

HRID 1388923Notes

Reaction equation

HRID 1388923 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=[O:16])=[C:10](C(O)=O)[C:9]=2[O:21][CH3:22])=[O:7])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[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])=[CH:10][C:9]=2[O:21][CH3:22])=[O:7])=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 204691265-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid

Product 1

HCID 13345722[5-(4-Chlorobenzoyl)-4-methoxy-1-methyl-1H-pyrrol-2-yl]acetic acidYield 81.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid (prepared from Example 1, Step E) is dissolved in 5 ml of trifluoroacetic acid (TFA) and heated to reflux under nitrogen. After about 45 minutes the reaction is substantially complete. It is cooled and concentrated in vacuo. The resultant residue is treated with 10 ml of water, and the precipitate is filtered, and dried to afford 925 mg (81.5%) of 5-(p-chlorobenzoyl)-4-methoxy-1-methylpyrrole-2-acetic acid, m.p. 142°.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen
  3. temperatureIt is cooled
  4. concentrationconcentrated in vacuo
  5. additionThe resultant residue is treated with 10 ml of water
  6. filtrationthe precipitate is filtered
  7. customdried

Sources & evidence

ORD record
ord-3e3c2c068d0041c9982d4dcbbb7c0fb4
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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