Potassium Hydroxide → 3-(1,5-Dimethyl-1H-pyrrol-2-yl)pyridine

HRID 462165Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=[C:3]1[CH:13]=O.O.NN.[OH-].[K+]>C(O)COCCOCCO>[CH3:1][N:2]1[C:3]([CH3:13])=[CH:4][CH:5]=[C:6]1[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 1-methyl-5-(3-pyridyl) pyrrole-2-carboxaldehyde (8.0 g, 43 mmoles), hydrazine hydrate (8.0 g, 160 mmoles) and potassium hydroxide (10.6 g of 85% pellets) in 80 ml triethyleneglycol is stirred at 125° L C for 75 min. during which time vigorous evolution of gas is observed. The temperature is then increased to 175° C and stirring continued until evolution of gas ceases. After cooling, the reaction mixture is extracted with 3 × 50 ml portions of diethyl ether. The combined ether layers are dried (anhydrous magnesium sulfate) and removed under vacuum. Fractional vacuum distillation of the residue provides the pure product.

Workup

stirringstirring
temperatureAfter cooling
extractionthe reaction mixture is extracted with 3 × 50 ml portions of diethyl ether
dry with materialThe combined ether layers are dried (anhydrous magnesium sulfate)
customremoved under vacuum
distillationFractional vacuum distillation of the residue
customprovides the pure product

Sources & evidence

ORD record: ord-2a3e65bce37441c0b52621b428767dd9
Source dataset: uspto-grants-1977_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04065561

Reaction notes

Loading…