Hydrazine hydrate (1:1) → HCID 23454144, compound

A solution of hydrazine hydrate (1.14 g; 22.8 mmol) and N-(1-methylhexyl)-2-phthalimidoacetamide (6.9 g; 22.8 mmol) in ethanol (50ml) was heated under reflux for 1 hour. It was then cooled to room temperature and evaporated in vacuo (Buchi, r.t.; then oil-pump, 0.5 mm/r.t./10 min.). The resultant semi-solid mixture was treated with dilutesulphuric acid (0.5 N; 85 ml) pre-cooled to 5°. The mixture was cooled to 0°, filtered and the precipitate mixed with more of the acid (2 N; 3×20 ml). The filtrate was kept in the refrigerator overnight and then filtered once more. After basification with sodium hydroxide solution (5 N; 40 ml), the mixture was extracted with dichloromethane (3×50 ml), the extracts dried (sodium sulphate) and evaporated in vacuo. The resultant oil was dried at 0.5 mm./r.t./0.5 h. T.l.c. (silica; chloroform:methanol: 3:2): 1 major spot, Rf. ca 0.5. I.v. and n.m.r. spectra were consistent with the structure. The product was purified as its hydrogen succinate.

1. temperatureunder reflux for 1 hour
2. customevaporated in vacuo (Buchi, r.t.
3. customoil-pump, 0.5 mm/r.t./10 min.
4. additionThe resultant semi-solid mixture was treated with dilutesulphuric acid (0.5 N; 85 ml)
5. temperaturepre-cooled to 5°
6. temperatureThe mixture was cooled to 0°
7. filtrationfiltered
8. additionthe precipitate mixed with more of the acid (2 N; 3×20 ml)
9. customwas kept in the refrigerator overnight
10. filtrationfiltered once more
11. extractionAfter basification with sodium hydroxide solution (5 N; 40 ml), the mixture was extracted with dichloromethane (3×50 ml)
12. dry with materialthe extracts dried (sodium sulphate)
13. customevaporated in vacuo
14. customThe resultant oil was dried at 0.5 mm
15. customr.t./0.5 h
16. customThe product was purified as its hydrogen succinate

ORD record

ord-d7336774e90e480badb5e16a17ede629

Source dataset

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04277498