Hydrochloric Acid → Ethyl 5-(p-chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate

HRID 1388921Notes

Reaction equation

HRID 1388921 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:18]([OH:20])=[O:19])[C:9]=2[O:21][CH3:22])=[O:7])=[CH:4][CH:3]=1.Cl.[CH2:26](O)[CH3:27]>>[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]([O:17][CH2:26][CH3:27])=[O:16])=[C:10]([C:18]([OH:20])=[O:19])[C:9]=2[O:21][CH3:22])=[O:7])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 204691265-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid

Product 1

HCID 13345721Ethyl 5-(p-chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate

Procedure

5-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid (478 mg) is suspended in 5 ml of absolute ethanol under nitrogen and heated to reflux. Concentrated hydrochloric acid (75 ml) is subsequently added and the reaction mixture is heated for another 20 minutes until all the solids are dissolved. The resulting solution is heated for an additional 10 minutes. Upon cooling, the product crystallizes out and is filtered, and dried in vacuo to afford 260 mg of ethyl 5-(p-chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate, m.p. 190 (dec.)

Workup

  1. temperatureheated to reflux
  2. temperaturethe reaction mixture is heated for another 20 minutes until all the solids
  3. dissolutionare dissolved
  4. temperatureThe resulting solution is heated for an additional 10 minutes
  5. temperatureUpon cooling
  6. customthe product crystallizes out
  7. filtrationis filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f402a5bb52b54c298c7ad1e6788dd51d
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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