Diethyl Ether → HCID 13145269, compound

To a stirred solution of 7.4 g. (50 mmoles) of 2-dimethylaminoisonicotinonitrile in 150 ml. of diethyl ether was added dropwise 33 ml. (100 mmoles) of a 3 M solution of methyl magnesium bromide under a nitrogen atmosphere. On completion, the reaction was allowed to stir at room temperature for 16 hours, and was then quenched by the careful addition of 80 ml. of 2 N hydrochloric acid. The aqueous phase was separated and the organic phase extracted further with 2 N hydrochloric acid (2×10 ml.). The combined acid extracts were neutralized with solid sodium carbonate and extracted with chloroform (5×50 ml.). The combined chloroform extracts were dried and concentrated to a brown oil. Distillation of the residue gave 5.0 g. (61%) of the product as an oil (b.p. 110° C./1 torr). On standing the oil crystallized, m.p. 37°-42° C.

1. customwas then quenched by the careful addition of 80 ml
2. customThe aqueous phase was separated
3. extractionthe organic phase extracted further with 2 N hydrochloric acid (2×10 ml.)
4. extractionextracted with chloroform (5×50 ml.)
5. dry with materialThe combined chloroform extracts were dried
6. concentrationconcentrated to a brown oil
7. distillationDistillation of the residue
8. customgave 5.0 g
9. customcrystallized

ORD record

ord-5fe042c1b46a4c97b0fc513598ead2f3

Source dataset

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04302464