Hydrazine hydrate (1:1) → Gyki-53405

To a suspension of 1.91 g (5.37 mmol) of 1-(4-nitrophenyl)-3-acetyl-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine (product of Example 27) in 40 ml of methanol about 0.2 g of Raney nickel catalyst and 1.4 ml (28 mmol) of 100% hydrazine hydrate were added, then the reaction mixture was stirred at 20°-25° C. for one hour. The starting nitro derivative was dissolved within 10-20 minutes. After filtering the filtrate was evaporated under reduced pressure, the white crystalline residue was washed with 30 ml of distilled water onto a filter, it was washed with 3×10 ml of distilled water and dried at 100 ° C. to give 1.50 g of a raw product, m.p. 218°-220° C. This raw product was purified by treating with 12 ml of hot isopropanol. After cooling it was filtered at 5° C., washed with 3×1 ml of isopropanol and dried at 100° C. to yield 1.40 g (77.35%) of a white crystalline powder, m.p. 221°-223° C. On the basis of analyses and spectra it was identical to the product of Example 15 obtained by a different process.

1. additionwere added
2. filtrationAfter filtering the filtrate
3. customwas evaporated under reduced pressure
4. washthe white crystalline residue was washed with 30 ml of distilled water onto a filter, it
5. washwas washed with 3×10 ml of distilled water
6. customdried at 100 ° C.
7. customto give 1.50 g of a raw product, m.p. 218°-220° C
8. customThis raw product was purified
9. additionby treating with 12 ml of hot isopropanol
10. temperatureAfter cooling it
11. filtrationwas filtered at 5° C.
12. washwashed with 3×1 ml of isopropanol
13. customdried at 100° C.

ORD record

ord-aa0e79419f3d4477aee8c9aabdd7c14e

Source dataset

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05604223