Water → (2-Hydroxymethylpyridin-3-yloxy)acetonitrile

HRID 1016415Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl.[OH:8][C:9]1[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=1.Cl[CH2:18][C:19]#[N:20].O>CS(C)=O>[OH:16][CH2:15][C:10]1[C:9]([O:8][CH2:18][C:19]#[N:20])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium carbonate (8.57 g, 0.062 mol) was stirred in DMSO (30 ml) under nitrogen at room temperature for 20 min. The mixture was cooled to 0° C. and 3-hydroxy-2-(hydroxymethyl)pyridine hydrochloride (5.0 g, 0.031 mol) was added. The slurry was stirred at 0° C. for 1.5 h before the addition of chloroacetonitrile (1.96 ml, 2.34 g, 0.031 mol). The mixture was allowed to warm to room temperature and stirred under nitrogen for 72 h. Water (100 ml) was added, and the resultant solution was extracted with dichloromethane (3×100 ml), the organic layers were combined, washed with water (1×100 ml) and saturated sodium chloride solution (1×100 ml), dried over magnesium sulfate and concentrated in vacuo to give the title compound as a dark brown solid (3.04 g). 1H NMR (250 MHz, CDCl3) δ 4.77 (2H, s), 4.85 (2H, s), 7.26-7.30 (2H, m), 8.32 (1H, m); MS (ES+) m/e, 165 [MH]+.

Workup

temperatureto warm to room temperature
extractionthe resultant solution was extracted with dichloromethane (3×100 ml)
washwashed with water (1×100 ml) and saturated sodium chloride solution (1×100 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-47ef4aa1ea654ec7ba41a717921416da
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476030B1

Reaction notes

Loading…