Hydrochloric Acid → HCID 18424343, compound

HRID 1282350Notes

Reaction equation

HRID 1282350 reaction equation
[C:1]([C:9]1[NH:13][C:12]([CH2:14][C:15]([O:17]CC)=[O:16])=[C:11](C(O)=O)[C:10]=1[CH3:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1.Cl.C(C1NC(CC(OCC)=O)=CC=1C)(=O)C1C=CC=CC=1.[OH-].[Na+]>[Cr]([O-])([O-])=O.[Cu+2].C(O)C>[C:1]([C:9]1[NH:13][C:12]([CH2:14][C:15]([OH:17])=[O:16])=[CH:11][C:10]=1[CH3:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 14798Sodium HydroxideHCID 54085546HCID 54085546, compoundHCID 54508799HCID 54508799, compound

Product 1

HCID 18424343HCID 18424343, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178505374HCID 178505374, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 4.13 g. (0.0131 mole) of ethyl 5-benzoyl-3-carboxy-4-methyl-pyrrole-2-acetate in 80 ml. of quinoline in the presence of a trace amount of copper chromite is heated at 180-183° C. for 5 hours. The mixture is poured into dilute hydrochloric acid and extracted three times with ether. The ether extracts are combined and washed successively with dilute hydrochloric acid, sodium bicarbonate solution and brine and then dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuo to give about 4 g. of semisolid ethyl 5-benzoyl-4-methylpyrrole-2-acetate which is used in the following hydrolysis procedure without further purification. The entire semisolid is dissolved in 20 ml. of ethanol and 20 ml. of 1N sodium hydroxide solution is added. The mixture is heated under reflux for 30 minutes. The solvent is then evaporated in vacuo, and the residue dissolved in water and washed with ether. The aqueous solution is acidified with dilute hydrochloric acid and the resulting crystalline solid (1.6 g., 50% yield) is collected by filtration and air-dried. The product, 5-benzoyl-4-methylpyrrole-2-acetic acid is recrystallized three times from acetone-water with charcoaling, m.p. 167-168° C.

Workup

  1. extractionextracted three times with ether
  2. washwashed successively with dilute hydrochloric acid, sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent is evaporated in vacuo
  5. customto give about 4 g
  6. dissolutionThe entire semisolid is dissolved in 20 ml
  7. temperatureThe mixture is heated
  8. temperatureunder reflux for 30 minutes
  9. customThe solvent is then evaporated in vacuo
  10. dissolutionthe residue dissolved in water
  11. washwashed with ether
  12. filtrationthe resulting crystalline solid (1.6 g., 50% yield) is collected by filtration
  13. customair-dried
  14. customThe product, 5-benzoyl-4-methylpyrrole-2-acetic acid is recrystallized three times from acetone-water with charcoaling, m.p. 167-168° C.

Sources & evidence

ORD record
ord-62dc30a3fcac47b2ac0f668ca1d92c26
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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