Hydrochloric Acid → 2-Azido-6-chloropyridine

To a 250 ml round-bottom flask equipped with a mechanical stirrer, a Claisen head and an addition funnel were added 2-chloro-6-hydrazinopyridine (4.00 g, 27.9 mmol), Et2O (20 mL) and concentrated hydrochloric acid (12 mL, 146 mmol). A solution of sodium nitrite (2.211 g, 32.0 mmol) in water (28 mL) was added dropwise to the cooled (0° C.) reaction mixture. The insoluble starting material gradually dissolved. After 2 h, the aqueous phase was extracted with ether (2×50 mL). The combined organic phase was dried over MgSO4, and concentrated in vacuo to provide the title compound as yellow crystals: LCMS m/z 155.14 [M+H]+.

1. customTo a 250 ml round-bottom flask equipped with a mechanical stirrer
2. temperaturecooled
3. custom(0° C.) reaction mixture
4. dissolutiongradually dissolved
5. extractionthe aqueous phase was extracted with ether (2×50 mL)
6. dry with materialThe combined organic phase was dried over MgSO4
7. concentrationconcentrated in vacuo

ORD record

ord-1f009bfbd0c34d87ad55aef5e540ebe1

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455638B2