Toluene → 5-(Chloromethyl)-2-methoxypyridine

To a solution of (6-methoxypyridin-3-yl)methanol (2) (537.8 g, 3.86 mol) obtained in Preparation Example 1 in dimethylformamide (1.6 L) was added dropwise thionyl chloride (310 mL, 4.25 mol) over a period of 1.3 hours while cooling in an ice bath under a nitrogen atmosphere. After stirring for 1 hour while cooling in an ice bath, toluene (5.4 L) and a 2N aqueous solution of sodium hydroxide (5.4 L) were added successively to the reaction mixture at 23° C. or below. The reaction mixture was stirred for about 10 minutes and then the aqueous layer was separated, the organic layer was washed with water (2.7 L). The organic layer was concentrated under reduced pressure to dryness, and then toluene (1.0 L) was added to the residue and azeotropic distillation was carried out to give 618.8 g of the title compound as a pale yellow oil (content 556.3 g, yield 91.4%).

1. temperaturewhile cooling in an ice bath under a nitrogen atmosphere
2. temperaturewhile cooling in an ice bath
3. stirringThe reaction mixture was stirred for about 10 minutes
4. customthe aqueous layer was separated
5. washthe organic layer was washed with water (2.7 L)
6. concentrationThe organic layer was concentrated under reduced pressure to dryness
7. additiontoluene (1.0 L) was added to the residue and azeotropic distillation

ORDレコード

ord-50d1b71d61b94d94aa2dcd6b7a418b7a

出典データセット

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07767812B2