Hydrazine hydrate (1:1) → 7,8-methylenedioxy-5-methyl-1-(4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one
Reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([C:10]2[CH:15]=[C:14]3[O:16][CH2:17][O:18][C:13]3=[CH:12][C:11]=2[CH:19]([CH3:24])[C:20](OC)=[O:21])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.[NH2:28][NH2:29]>COCCO>[CH2:17]1[O:16][C:14]2=[CH:15][C:10]3[C:8]([C:7]4[CH:25]=[CH:26][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)=[N:29][NH:28][C:20](=[O:21])[CH:19]([CH3:24])[C:11]=3[CH:12]=[C:13]2[O:18]1Participants
Procedure
A mixture of methyl 2-(2-(4-nitrobenzoyl)-4,5-methylenedioxyphenyl)propionate (211 mg, 0.59 mmol), hydrazine hydrate (0.15 mL, 2.4 mmol), and 2-methoxyethanol (6 mL) was heated to reflux for 72 h. The solvent was removed in vacuo and the crude product was purified by chromatography to yield 7,8-methylenedioxy-5-methyl-1-(4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one which was treated with excess amount of hydrazine and Raney Ni for 1 h. The reaction was then allowed to settled and liquid phase was decanted. The solvent was then removed and residue obtained was purified by chromatography (10% acetone in CH2Cl2) to yield the product (5 mg). 1H NMR (CDCl3) 8.44 (s, 1H), 7.43 (d, J=8.7, 2H), 6.86 (s, 1H), 6.68 (d, J=8.7, 2H), 6.65 (s, 1H), 6.04 (s, 1H), 6.00 (s, 1H), 4.83 (b, 2H), 3.29 (q, J=6.8, 1H), 1.59 (d, J=6.8, 3H).
Workup
- temperaturewas heated
- temperatureto reflux for 72 h
- customThe solvent was removed in vacuo
- customthe crude product was purified by chromatography
Sources & evidence
- ORD record
- ord-bb6855e2ed034bb597cb3be22bcbe4b1
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05891871
Reaction notes
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