Hydrochloric Acid → HCID 20373228, compound

HRID 863640Notes

Reaction equation

HRID 863640 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[NH:12][C:11](C(O)=O)=[C:10]([CH2:16][C:17]([OH:19])=[O:18])[C:9]=2[CH3:20])=[O:7])=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1.Cl>>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:8]2[NH:12][CH:11]=[C:10]([CH2:16][C:17]([OH:19])=[O:18])[C:9]=2[CH3:20])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 21545870HCID 21545870, compound

Product 1

HCID 20373228HCID 20373228, compound

Procedure

A solution of 1.4 g. (0.004 mole) of 5-(ρ-chlorobenzoyl)-4-methyl-2-carboxypyrrole-3-acetic acid in 25 ml. quinoline is heated overnight at 160° C. under nitrogen. The reaction is poured into ice acidified with hydrochloric acid. The mixture is extracted with chloroform, and the organic phase is extracted with a saturated solution of sodium bicarbonate. The basic solution is made acidic with dilute hydrochloric acid, and the resulting solid, 5-(ρ-chlorobenzoyl)-4-methylpyrrole-3-acetic acid, is filtered and purified by recrystallization from isopropyl alcohol, M.P. 145°-147° C.

Workup

  1. additionThe reaction is poured into ice
  2. extractionThe mixture is extracted with chloroform
  3. extractionthe organic phase is extracted with a saturated solution of sodium bicarbonate
  4. filtrationthe resulting solid, 5-(ρ-chlorobenzoyl)-4-methylpyrrole-3-acetic acid, is filtered
  5. custompurified by recrystallization from isopropyl alcohol, M.P. 145°-147° C.

Sources & evidence

ORD record
ord-8db69ea478bc41f0b44b574b1c450121
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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