Hydrochloric Acid → 4-[5-(Pent-4-en-1-yl)pyridin-2-yl]benzonitrile
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:19][N:20](C)C=O.[Cu]C#N.Cl>[Fe](Cl)(Cl)Cl.O>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:19]#[N:20])=[CH:3][CH:4]=2)=[N:9][CH:10]=1)[CH2:15][CH2:16][CH:17]=[CH2:18]Participants
Conditions
- Temperature
- 180 °C
Procedure
A suspension of 5.59 g of 2-(p-bromophenyl)-5-(4-pentenyl)pyridine, 4 ml of dimethylformamide and 1.98 g of copper(I) cyanide was heated to 180° C. for 3 hours while stirring. The brown reaction mixture was then cooled to room temperature, subsequently poured into a mixture of 3.67 g of iron(III) chloride, 36.7 ml of water and 0.245 ml of concentrated hydrochloric acid and stirred at 55° C. for a further 1 hour. Thereafter, the mixture was cooled and partitioned between methylene chloride and water. The organic phase was washed with water, dried over sodium sulphate and filtered. The filtrate was evaporated and the residue was purified by chromatography on 250 g of silica gel with 2.5 l of methylene chloride under slight pressure. The p-[5-(4-pentenyl)-2-pyridyl]benzonitrile obtained had a m.p. (C--N) of -12° C. and could not be crystallized by cooling to below -70° C.
Workup
- temperatureThe brown reaction mixture was then cooled to room temperature
- stirringstirred at 55° C. for a further 1 hour
- temperatureThereafter, the mixture was cooled
- custompartitioned between methylene chloride and water
- washThe organic phase was washed with water
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customThe filtrate was evaporated
- customthe residue was purified by chromatography on 250 g of silica gel with 2.5 l of methylene chloride under slight pressure
Sources & evidence
- ORD record
- ord-97c08aec5db949f9bf1202d704782855
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04898455
Reaction notes
Loading…