Pyridine → HCID 178527120, compound

Thionyl chloride (2.55 ml, 0.035 mol) was added dropwise to a mixture of N'-hydroxy-(3,4-dihydro-2-naphthalenyl)ethanimidamide (6.5 g, 0.032 mol) and pyridine (5.18 ml, 0.064 mol) in dry dichloromethane (100 ml) at 0° C. Upon completion of the addition, the reaction mixture was concentrated under reduced pressure, placed in an ice bath, diluted with deionized water (50 ml), extracted with diethyl ether (3×50 ml), filtered, dried over MgSO4 and concentrated under reduced pressure to give the crude title compound as a red-brown solid. The solid was triturated with diethyl ether (3×50 ml), dissolved in boiling diethyl ether (100 ml), vacuum filtered and recrystallized from diethyl ether (75 ml) to yield 1.14 g (14.4% yield) of pure product, m.p. 118°-120.5° C.

1. additionUpon completion of the addition
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. customplaced in an ice bath
4. additiondiluted with deionized water (50 ml)
5. extractionextracted with diethyl ether (3×50 ml)
6. filtrationfiltered
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customto give the crude title compound as a red-brown solid
10. customThe solid was triturated with diethyl ether (3×50 ml)
11. dissolutiondissolved
12. filtrationfiltered
13. customrecrystallized from diethyl ether (75 ml)

ORD record

ord-d41182b3879a462b90c2d0f937f37629

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04910019