Aluminium lithium hydride → HCID 58009138, Verbindung

Temperatur

0 °C

A −50° C. solution of ethyl 6-chloro-4-(ethylamino)nicotinate (3.9 g, 17 mmol) in THF (50 mL) was treated with LiAlH4 (3.6 g, 95 mmol), allowed to warm to 0° C. and stirred for 1 h. The mixture was quenched with 10% NaOH (3.6 mL), filtered and the filtrate treated with water and extracted with EtOAc (3×). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo to provide (6-chloro-4-(ethylamino)pyridin-3-yl)methanol (2.5 g, 79% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.84 (s, 1H), 6.55 (s, 1H), 6.17 (m, 1H), 5.25 (t, J=5.2 Hz, 1H), 4.44 (q, J=7.2 Hz, 2H), 3.23 (m, 2H), 1.23 (t, J=7.2 Hz, 3H).

1. customThe mixture was quenched with 10% NaOH (3.6 mL)
2. filtrationfiltered
3. additionthe filtrate treated with water
4. extractionextracted with EtOAc (3×)
5. washThe combined organics were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-512a0e942f83458ea7604de4fc5adf82

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08940756B2