(6-Dimethylamino-3-nitro-2-pyridyl)acetonitrile → N,N-dimethyl-1H-pyrrolo[3,2-b]pyridin-5-amine

A mixture of (6-dimethylamino-3-nitro-2-pyridyl)-acetonitrile (Compound 5c,2.06 g, 10.0 mmol), Raney nickel (0.70 g, washed thoroughly with absolute ethanol), and absolute ethanol/acetic acid (4:1, 50 mL) was shaken under ahydrogen atmosphere (3 atm) for 3 hours. The resulting mixture was filteredthrough diatomaceous earth (Celite (trademark)), and the filtrate was evaporated under reduced pressure. The residual oil was dissolved in water(25 mL), the pH was adjusted to 10 with sodium carbonate, and the mixture was extracted with methylene chloride (3×25 mL). These extracts werecombined, dried (MgSO4), and evaporated under reduced pressure to yield an oil. This oil was dissolved in ethyl acetate (10 mL), and this solution was passed through an alumina (basic) filter (approximately 100 g) followed by ethyl acetate (1500 mL). The resulting filtrate was evaporated under reduced pressure to yield Compound 7j (0.44 g, 2.73 mmol,27%) as a white solid: mp, 149.0°-151.0° C.; IR

1. washwashed thoroughly with absolute ethanol), and absolute ethanol/acetic acid (4:1, 50 mL)
2. customthe filtrate was evaporated under reduced pressure
3. dissolutionThe residual oil was dissolved in water(25 mL)
4. extractionthe mixture was extracted with methylene chloride (3×25 mL)
5. dry with materialdried (MgSO4)
6. customevaporated under reduced pressure
7. customto yield an oil
8. filtrationfilter (approximately 100 g)
9. customThe resulting filtrate was evaporated under reduced pressure

ORD record

ord-1316564a67604640995d7286f518c6fd

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05051412