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

HRID 1275294
Notes
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Reaction equation

HRID 1275294 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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

Conditions

Temperature
200 °C

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 hours at 200° C., then for 30 minutes 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. distillationThe quinoline is distilled off in vacuo
  2. dissolutionThe residue is dissolved in ether
  3. washwashed successively with dilute hydrochloric acid, dilute sodium hydroxide, and brine
  4. dry with materialdried over magnesium sulfate
  5. customand the solvent evaporated in vacuo
  6. customto give a brown oily residue which
  7. customcrystallizes
  8. customIt is recrystallized from methanol
  9. customsublimed at 150° C.
  10. customrecrystallized from hexane

Sources & evidence

ORD record
ord-9ca4fe12717d468fac40b2fd8680bca0
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06160003

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes