Quinoline → Ethyl 1,4 dimethyl-5-(rho-toluoyl)-pyrrole-2-acetate

HRID 1606171Notes

Reaction equation

HRID 1606171 reaction equation
C([C:4]1[C:8]([CH3:9])=[C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[O:11])[N:6]([CH3:19])[C:5]=1[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(O)=O.N1C2C(=CC=CC=2)C=CC=1>[Cr]([O-])([O-])=O.[Cu+2]>[CH3:19][N:6]1[C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[O:11])=[C:8]([CH3:9])[CH:4]=[C:5]1[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 18424327Ethyl 3-carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetate

Product 1

HCID 18424313Ethyl 1,4 dimethyl-5-(rho-toluoyl)-pyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 178505374HCID 178505374, compoundCatalyst

Procedure

A solution of 33.0 g. (0.096 mole) of ethyl 3-carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetate in 200 ml. of quinoline with 0.1 g. copper chromite added is heated under nitrogen for 6 hr. at 200°C., then for 30 min. at 220°C. The quinoline is distilled off in vacuo. The residue is dissolved in ether and washed successively with dilute hydrochloric acid, dilute sodium hydroxide, and brine; dried over magnesium sulfate; and the solvent evaporated in vacuo to give a brown oily residue which crystallizes. It is recrystallized from methanol, sublimed at 150°C. (0.025 mm/Hg) and recrystallized from hexane to give ethyl 1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetate as a white solid, m.p. 90°-93°C.

Workup

  1. temperatureis heated under nitrogen for 6 hr
  2. distillationThe quinoline is distilled off in vacuo
  3. dissolutionThe residue is dissolved in ether
  4. washwashed successively with dilute hydrochloric acid, dilute sodium hydroxide, and brine
  5. dry with materialdried over magnesium sulfate
  6. customand the solvent evaporated in vacuo
  7. customto give a brown oily residue which
  8. customcrystallizes
  9. customIt is recrystallized from methanol
  10. customsublimed at 150°C.
  11. customrecrystallized from hexane

Sources & evidence

ORD record
ord-a556425d5fe742adb933557c74778053
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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