HCID 22405287, compound → 1,3,4,5-Tetrahydro-8-methyl-2H-1,5-benzodiazepin-2-one

A mixture of N-(2-ethoxycarbonylethyl)-4-methyl-2-nitroaniline (11.25 g) and iron powder (12.45 g) in a mixture of methanol (70 ml) and acetic acid (7 ml) was refluxed for 1 hour and the solution was cooled to ambient temperature. The mixture was filtered through celite and the filtrate was evaporated in vacuo. The residue was dissolved with chloroform (50 ml) and the solution was basified with saturated sodium bicarbonate aqueous solution. The solution was filtered through celite and the organic layer was washed with brine. The solution was dried over magnesium sulfate and the solvent was removed. A mixture of the residue (8.00 g) in a mixture of concentrated hydrochloric acid (16 ml) and water (12 ml) was refluxed for 1 hour and the solution was cooled to ambient temperature. The mixture was basified with concentrated ammonium hydroxide and then the resulting solution was extracted with chloroform. Drying over magnesium sulfate, filtering and the removal of solvents afforded a crude product. The crude product was triturated with diethyl ether - isopropyl ether (1:1) to give 8-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (1.26 g) as a brown powder.

1. temperaturewas refluxed for 1 hour
2. filtrationThe mixture was filtered through celite
3. customthe filtrate was evaporated in vacuo
4. dissolutionThe residue was dissolved with chloroform (50 ml)
5. filtrationThe solution was filtered through celite
6. washthe organic layer was washed with brine
7. dry with materialThe solution was dried over magnesium sulfate
8. customthe solvent was removed
9. additionA mixture of the residue (8.00 g)
10. additionin a mixture of concentrated hydrochloric acid (16 ml) and water (12 ml)
11. temperaturewas refluxed for 1 hour
12. temperaturethe solution was cooled to ambient temperature
13. extractionthe resulting solution was extracted with chloroform
14. dry with materialDrying over magnesium sulfate
15. filtrationfiltering
16. customthe removal of solvents
17. customafforded a crude product
18. customThe crude product was triturated with diethyl ether - isopropyl ether (1:1)

ORD record

ord-879d11ac84554005b8862850a9437b3b

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05521170