HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroform → 2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine | HCID 737823 | — |
| Product | 2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride | HCID 11694258 | 69% |
Reaction Steps
To a solution of crude 2-hydroxymethyl-3,5-dimethyl-4-methoxypyridine (23.41 g, 0.41 mol) in CHCl3 (70 ml) was added SO2Cl2 (30 ml, 0.42 mol) at ice bath temperature. The reaction mixture was refluxed for 2 h and cooled to rt. Evaporation of the solvent in vacuo gave a dark brown solid. Recrystallization from isopropanol-ether gave 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride (14) (21.6 g, 69%) as a white solid; mp 135-136° C. For previous syntheses see references cited in Brandstrom et al., Acta Chemica Scandinavia 43: 536-548, 1989 and GB 2134523.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05670526 |
| Source dataset | uspto-grants-1997_09 |
| ORD ID | ord-0198fff3c44b4f0c8fc972b14149e244 |
| Source note | uspto-grants-1997_09 |