Methanol → 6-(Methylamino)nicotinaldehyde

Temperatur

-78 °C

To 6-(methylamino)-3-pyridinecarbonitrile (D94) (0.1 g, 0.752 mmol) in toluene (10 mL) cooled to −78 C under argon was added Dibal-H (1.88 mL, 1M solution in toluene, 11.2 mmol) dropwise. The reaction was stirred at −78° C. and then allowed to warm to room temperature overnight. MeOH (0.47 mL) and 2 M H2SO4 (1.42 mL) were added and mixture was stirred for 1.5 h then concentrated in vacuo. The residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried and concentrated to give the title compound (0.067 g). δH (CDCl3, 400 MHz) 9.78 (1H, s), 8.52 (1H, d), 7.92 (1H, dd), 6.45 (1H, d), 5.38 (1H, br.s), 3.04 (3H, d). MS (ES): MH+ 137.1.

1. temperatureto warm to room temperature overnight
2. stirringmixture was stirred for 1.5 h
3. concentrationthen concentrated in vacuo
4. customThe residue was partitioned between water and EtOAc
5. extractionThe aqueous layer was extracted with EtOAc
6. customthe combined organic layers were dried
7. concentrationconcentrated

ORD-Eintrag

ord-1736eaf9a54f42d4a0e5b0f6d192c1b8

Quelldatensatz

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07700599B2