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

HRID 1275294Notes

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

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

distillationThe quinoline is distilled off in vacuo
dissolutionThe residue is dissolved in ether
washwashed successively with dilute hydrochloric acid, dilute sodium hydroxide, and brine
dry with materialdried over magnesium sulfate
customand the solvent evaporated in vacuo
customto give a brown oily residue which
customcrystallizes
customIt is recrystallized from methanol
customsublimed at 150° C.
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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