3-Methylpyridine-2-carbonitrile → (3-Methylpyridin-2-yl)methanamine

3-Methylpyridine-2-carbonitrile (2.0 g, 16.95 mmol) in THF (50 ml) at 0° C. was added to a solution of lithium aluminium hydride (16.95 ml, 1 M in THF) and the mixture allowed to warm to RT overnight. The reaction was cooled to 0° C. and quenched with ethyl acetate (2.5 ml). Sodium hydroxide (2.5 ml, 1 M) was added and the mixture stirred at RT for 1 h, then filtered through Celite®. The filtrate was extracted with ethyl acetate (2×20 ml) and the combined organics washed with brine (50 ml) and dried (MgSO4). The crude material was purified by chromatography (0–5% MeOH in CH2Cl2+1% NH3) to yield a yellow oil (282 mg).

1. temperatureThe reaction was cooled to 0° C.
2. customquenched with ethyl acetate (2.5 ml)
3. additionSodium hydroxide (2.5 ml, 1 M) was added
4. filtrationfiltered through Celite®
5. extractionThe filtrate was extracted with ethyl acetate (2×20 ml)
6. washthe combined organics washed with brine (50 ml)
7. dry with materialdried (MgSO4)
8. customThe crude material was purified by chromatography (0–5% MeOH in CH2Cl2+1% NH3)

ORD record

ord-fc025b955beb41b0af013e21e22aa4f7

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183294B2