Hydrochloric Acid → HCID 571501, compound
Reaction equation
[Li].[CH:2]1(Br)[CH2:4][CH2:3]1.[C:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)#N.[Cl-].[NH4+].Cl.CC[O:19]CC>>[N:11]1[CH:12]=[CH:13][C:8]([C:6]([CH:2]2[CH2:4][CH2:3]2)=[O:19])=[CH:9][CH:10]=1Participants
Procedure
To a suspension of 6.0 g (0.83 mole) of lithium wire in 250 ml of ether under argon, is added a solution of 50 g (0.41 mole) of cyclopropyl bromide in 50 ml of ether. A gentle reflux is maintained throughout the addition. Stir for 15 hr. at room temperature. The reaction mixture is added slowly to a solution of 29 g (0.28 mole) of 4-cyanopyridine in 200 ml of ether at -70° C. and stirred at -70° C. for 1 hr. and then allowed to warm to room temperature. Stir at room temperature for 2 hr. then add 70 ml of saturated ammonium chloride and 150 ml of 6N HCl. Extract the reaction mixture with two 500 ml portions of ether. The aqueous portion is made basic with potassium carbonate and extracted with three 500 ml portions of ethylacetate. The combined extracts are dried over magnesium sulfate and concentrated in vacuo. The residue is distilled under vacuum to provide the title compound--bp 65° C. at 0.03 mm Hg.
Workup
- temperatureA gentle reflux
- temperatureis maintained throughout the addition
- customat room temperature
- stirringstirred at -70° C. for 1 hr
- stirringStir at room temperature for 2 hr
- extractionExtract the reaction mixture with two 500 ml portions of ether
- extractionextracted with three 500 ml portions of ethylacetate
- dry with materialThe combined extracts are dried over magnesium sulfate
- concentrationconcentrated in vacuo
- distillationThe residue is distilled under vacuum
Sources & evidence
- ORD record
- ord-8d3e709888c94457a3b26296236b079d
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04596872
Reaction notes
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