Methanol → HCID 13068178, compound

HRID 67117Notes

Reaction equation

HRID 67117 reaction equation
[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([O:19]C)=[O:18])[C:12]2=[CH:11][C:10]=1[Cl:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]2=[CH:11][C:10]=1[Cl:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 13068177methyl 5-benzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

Product 1

HCID 13068178HCID 13068178, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 5-benzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate (1.10 g.) in 30 ml. of methanol containing 2 molar equivalents potassium carbonate in 10 ml. of water is heated at reflux temperature for three hours. The methanol is removed in vacuo and water is added to the residue. The solution is extracted with ethyl acetate, the aqueous phase is cooled to 0° and made acidic with 20% hydrochloric acid. The solid which precipitates is collected by filtration, washed with cold water and dried in vacuo. The residue is crystallized from methanol-water to give 5-benzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid, m.p. 190° C.

Workup

  1. temperatureat reflux temperature for three hours
  2. customThe methanol is removed in vacuo and water
  3. additionis added to the residue
  4. extractionThe solution is extracted with ethyl acetate
  5. temperaturethe aqueous phase is cooled to 0°
  6. customThe solid which precipitates
  7. filtrationis collected by filtration
  8. washwashed with cold water
  9. customdried in vacuo
  10. customThe residue is crystallized from methanol-water

Sources & evidence

ORD record
ord-6b8579df8872475aa6cf4e82033c7ce0
Source dataset
uspto-grants-1982_08
Patent number
US04344943

Reaction notes

Loading…