Sodium Bicarbonate → 2-Chloro-5-(chloromethyl)pyridine

The mother liquor remaining after separation of the above crop of crystals was concentrated and the insoluble residue was dissolved in EtOH, diluted with toluene and concentrated. The above procedure was carried out for a total of 3 times to recover 9.04 g of crude 6-chloro-3-pyridylmethyl chloride as an oil. (5) In 50 ml of water was suspended 15.0 g (0.076 mole) of 6-chloro-3-pyridylmethyl chloride hydrochloride and the suspension was adjusted to pH about 8 with a saturated aqueous solution of sodium hydrogen carbonate. The resulting mixture was extracted with ether (100 ml×3) and dried over MgSO4. The ether was then distilled off under reduced pressure to give a crystalline residue. After addition of hexane, the crystals were recovered by filtration, washed with hexane and dried to give 11.0 g of 6-chloro-3-pyridylmethyl chloride as white prisms.

1. customafter separation of the above crop of crystals
2. concentrationwas concentrated
3. dissolutionthe insoluble residue was dissolved in EtOH
4. additiondiluted with toluene
5. concentrationconcentrated
6. customto recover 9.04 g of crude 6-chloro-3-pyridylmethyl chloride as an oil
7. extractionThe resulting mixture was extracted with ether (100 ml×3)
8. dry with materialdried over MgSO4
9. distillationThe ether was then distilled off under reduced pressure
10. customto give a crystalline residue
11. filtrationthe crystals were recovered by filtration
12. washwashed with hexane
13. customdried

ORD record

ord-8f6e7dd461c64029b2afcec085ad2e34

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06124297