Ethanol → 4-phenyl-1H-pyrrole-2-carboxylic acid

HRID 1981033Notes

Reaction equation

HRID 1981033 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[NH:11][CH:12]=2)=[CH:4][CH:3]=1.C(O)C>[Pd].C(N(CC)CC)C>[C:5]1([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[NH:11][CH:12]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 128970994-(4-Chlorophenyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 128971004-phenyl-1H-pyrrole-2-carboxylic acidYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

4-(4-Chlorophenyl)pyrrole-2-carboxylic acid (0.6 g.) was hydrogenated over 200 mg. of 5% Pd/C in 50 ml. of ethanol for approximately 16 hours at 50 p.s.i. An additional 200 ml. of catalyst and 1 ml. of triethylamine was added and hydrogenation continued for 3 hours at 50 p.s.i. The catalyst was recovered by filtration, and the mother liquor concentrated to dryness to yield 4-phenylpyrrole-2-carboxylic acid [400 mg., m.p. 226°-228° C. (dec.), m/e 187]. For analysis, the product was recrystallized from acetone/hexane [240 mg., m.p. 227°-229° C. (dec.)].

Workup

  1. filtrationThe catalyst was recovered by filtration
  2. concentrationthe mother liquor concentrated to dryness

Sources & evidence

ORD record
ord-884342a0ad7942f0bc23372b7cae78c6
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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