Ethanol → 7,8-Methylenedioxy-1-(3-methyl-4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

HRID 442686

Reaktionsgleichung

Reaktionsgleichung von HRID 442686
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([C:15](=O)[C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=3)=[C:6]([CH2:10][C:11](OC)=[O:12])[CH:7]=2)[O:2]1.O.[NH2:28][NH2:29].C(O)C>>[CH2:1]1[O:2][C:3]2=[CH:4][C:5]3[C:15]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=4)=[N:29][NH:28][C:11](=[O:12])[CH2:10][C:6]=3[CH:7]=[C:8]2[O:9]1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 53912114Methyl 4,5-Methylenedioxy-2-(3-methyl-4-nitrobenzoyl)phenylacetate

Produkt 1

HCID 538477727,8-Methylenedioxy-1-(3-methyl-4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

Versuchsvorschrift

The title compound was prepared from methyl 4,5-methylenedioxy-2-(3-methyl-4-nitrobenzoyl)phenylacetate (1.4 g, 3.9 mmol) and hydrazine hydrate (1.0 mL, 18 mmol) in ethanol (25 mL) as a yellow solid (0.65 g, 1.9 mmol, 49%), mp: 275°-277° C. 1H NMR (CDCl3) 8.65 (s, 1H), 8.02 (d, J=8.5, 1H), 7.62 (s, 1H), 7.56 (d, J=8.5, 1H), 6.85 (s, 1H), 6.56 (s, 1H), 6.06 (s, 2H), 3.48 (s, 2H), 2.64 (s, 3H). Anal. Calcd. for C17H13N3O5 : C, 60.18; H, 3.86; N, 12.38. Found: C, 60.22; H, 3.83; N, 12.28.

Quellen und Nachweise

ORD-Eintrag
ord-976b0673e731470d8da254df5a19052d
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891871

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