Hydrochloric Acid → HCID 12897085, compound

HRID 1981022Notes

Reaction equation

HRID 1981022 reaction equation
[C:1]1([C:7]2[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>C(Cl)Cl>[C:1]1([C:7]2[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][NH:10][C:11]=2[C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 5142464Methyl 4-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 12897085HCID 12897085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-phenylpyrrole-3-carboxylate (920 mg., 4.6 mmoles) and benzoyl chloride (0.53 ml., 4.6 mmoles) were combined in 50 ml. methylene chloride and stirred under nitrogen at room temperature. Stannic chloride (1.15 ml., 10 mmoles) was added. The resulting solution was stirred for 1.5 hours. Hydrochloric acid (1N, 25 ml.) was added slowly. The mixture was stirred for 10 minutes, the methylene chloride layer separated, back-washed with two 20 ml. portions of water, approximately 50 mg. of solids removed by filtration, and the filtrate evaporated to dryness. Recrystallization of the residue from acetone afforded purified methyl 4-phenyl-5-benzoylpyrrole-3-carboxylate (673 mg., m.p. 201°-203° C.).

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. customthe methylene chloride layer separated
  3. washback-washed with two 20 ml
  4. customof solids removed by filtration
  5. customthe filtrate evaporated to dryness
  6. customRecrystallization of the residue from acetone
  7. customafforded
  8. custompurified methyl 4-phenyl-5-benzoylpyrrole-3-carboxylate (673 mg., m.p. 201°-203° C.)

Sources & evidence

ORD record
ord-f5403b9fbfe44780b4f3338677d9d767
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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