Hydrochloric Acid → HCID 55278964, compound

Triphenylphosphine (0.81 g, 3.1 mmol) was added to a solution of the above 3-azidomethyl-4-chloro-pyridine (0.47 g, 3.1 mmol) in anhydrous THF (10 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was then diluted with NH4OH (3 mL) and stirred for another 3 h. 3M NaOH was then added to the reaction mixture and stirred for 1 h. The mixture was acidified to pH 2 by adding 4M HCl solution. The mixture was diluted with ether and the layers were separated. The aqueous layer was extracted with ether and then basified with 2M NaOH solution. The aqueous solution was extracted with CH2Cl2 (×3). The combined organic phase was dried over MgSO4 and concentrated in vacuo to afford a pale yellow oily solid. This product was diluted with ether and filtered. The filtrated was concentrated in vacuo to afford a pale yellow oil. The crude product was purified by silica gel column chromatography using 20:1 CH2Cl2:MeOH as an eluent to afford 0.21 g (53%) of 3-aminomethyl-4-chloropyridine as a colorless oil.

1. stirringstirred for another 3 h
2. stirringstirred for 1 h
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with ether
5. extractionThe aqueous solution was extracted with CH2Cl2 (×3)
6. dry with materialThe combined organic phase was dried over MgSO4
7. concentrationconcentrated in vacuo
8. customto afford a pale yellow oily solid
9. filtrationfiltered
10. concentrationThe filtrated was concentrated in vacuo
11. customto afford a pale yellow oil
12. customThe crude product was purified by silica gel column chromatography

ORD record

ord-4e0d72c054124d75b2701a7d569ae509

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601714B2