Pyridine → 4-Pentyl-2-cyanopyridine

To (1-Oxy-pyridin-4-yl)-methanol (5g, 0.04 mol) in a solution of dichloromethane (10 mL) and pyridine (10 mL) was added acetic anhydride (12.2 mL, 0.12 mol) and the reaction mixture was stirred for 16 h at room temperature. The reaction mixture was then poured into water and extracted with dichloromethane (200 mL) and then washed with brine (100 mL). The crude product obtained (4.27 g, 64%) was taken without purification for the next reaction. To the crude product (4.27 g, 25.6 mmol) in DCM (25 mL) and trimethylsilyl cyanide (3.40 mL, 25.6 mmol), dimethylcarbamyl chloride (2.35 mL, 25.6 mmol) was added slowly and then the reaction mixture was stirred at room temperature over night. Aqueous potassium carbonate (100 mL, 10%) was added and stirred for 10 minutes. Extraction with ethyl acetate followed by removal of solvent resulted in crude product which was purified on silica gel column chromatography using 50% ethyl acetate in hexanes to obtain cyanopyridine 10a (R9=acetoxymethylene) (2.37 g, 48%).

1. extractionextracted with dichloromethane (200 mL)
2. washwashed with brine (100 mL)
3. customThe crude product obtained (4.27 g, 64%)
4. customwas taken without purification for the next reaction
5. stirringthe reaction mixture was stirred at room temperature over night
6. stirringstirred for 10 minutes
7. extractionExtraction with ethyl acetate
8. customfollowed by removal of solvent
9. customresulted in crude product which
10. customwas purified on silica gel column chromatography

ORD record

ord-65d1cde6c86844199d526dd3a8caed15

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199105B2