Aluminium lithium hydride → HCID 58009138, compound

Temperature

0 °C

To a solution of ethyl 6-chloro-4-(ethylamino)nicotinate (3.9 g, 17 mmol) in anhydrous THF (50 mL) was added LiAlH4 (3.6 g, 95 mmol) at −50° C., then the resulting mixture was allowed to warm to 0° C. and stirred for 1 h. Then the mixture was quenched by the addition of 10% aq NaOH solution (3.6 mL). The mixture was filtered and the filtrate was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo to provide to (6-chloro-4-(ethylamino)pyridin-3-yl)methanol (2.5 g, 79% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.84 (s, 1 H), 76.55 (s, 1 H), 6.17 (m, 1 H), 5.25 (t, J=5.2 Hz, 1 H), 4.44 (q, J=7.2 Hz, 2 H), 3.23 (m, 2H), 1.23 (t, J=7.2 Hz, 3H).

1. customThen the mixture was quenched by the addition of 10% aq NaOH solution (3.6 mL)
2. filtrationThe mixture was filtered
3. customthe filtrate was partitioned between water and EtOAc
4. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
5. washThe combined organics were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-a436b6fe61434b909ec8d4fabf9bab1c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188113B2