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

HRID 442687Notes

Reaction equation

HRID 442687 reaction equation
[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])=[CH:18][C:17]=3[Cl:25])=[C:6]([CH2:10][C:11](OC)=[O:12])[CH:7]=2)[O:2]1.O.[NH2:28][NH2:29].C(O)C>>[Cl:25][C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:16]=1[C:15]1[C:5]2[CH:4]=[C:3]3[O:2][CH2:1][O:9][C:8]3=[CH:7][C:6]=2[CH2:10][C:11](=[O:12])[NH:29][N:28]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 54561972Methyl 2-(2-Chloro-4-nitrobenzoyl)-4,5-methylenedioxyphenylacetate

Product 1

HCID 540649381-(2-Chloro-4-nitrophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

Procedure

The title compound was prepared from methyl 4,5-methylenedioxy-2-(2-chloro-4-nitrobenzoyl)phenylacetate (11 g, 29 mmol) and hydrazine hydrate (5.0 mL, 88 mmol) in ethanol (60 mL) as a yellow solid (1.4 g, 3.9 mmol, 13%), mp: 202°-204° C. 1H NMR (CDCl3) 8.64 (s, 1H), 8.29-8.26 (m, 2H), 7.82 (d, J=8.2, 1H), 6.84 (s, 1H), 6.28 (s, 1H), 6.02 (s, 2H), 3.59 (s, 2H). Anal. Calcd. for C16H10N3O5.(1/2)H2O: C, 52.12; H, 3.01; N, 11.40. Found: C, 52.50; H, 3.36; N, 10.35.

Sources & evidence

ORD record
ord-d5613511cff4411783e2edddf0d1cfed
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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