Hydrazine hydrate (1:1) → 5-Methyl-7,8-methylenedioxy-1-phenyl-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

HRID 442675Notes

Reaction equation

HRID 442675 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]2[O:15][CH2:16][O:17][C:12]2=[CH:11][C:10]=1[CH:18]([CH3:23])[C:19](OC)=[O:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:25][NH2:26]>COCCO>[CH3:23][CH:18]1[C:10]2[CH:11]=[C:12]3[O:17][CH2:16][O:15][C:13]3=[CH:14][C:9]=2[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:26][NH:25][C:19]1=[O:20]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53747217Methyl 2-(2-Benzoyl-4,5-methylenedioxyphenyl)propionate

Product 1

HCID 545669615-Methyl-7,8-methylenedioxy-1-phenyl-3,5-dihydro-2,3-benzodiazepin-4(4H)-oneYield 18%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of methyl 2-(2-benzoyl-4,5-methylenedioxyphenyl)propionate, hydrazine hydrate (0.45 mL), and 2-methoxyethanol (6 mL) was heated to reflux for 20 h. The solvent was then removed in vacuo and the residue was purified by a flash chromatography (EtOAc:Hex=1:1.5) to yield the product as a white solid (62 mg, 18%), mp, 206°-209° C. 1H NMR (CDCl3) 8.45 (s, 1H), 7.62 (m, 2H), 7.45 (m, 3H), 6.88 (s, 1H), 6.63 (s, 1H), 6.05 (s, 1H), 6.00 (s, 1H), 3.29 (q,J=6.7, 1H), 1.62 (d,J=6.7, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. customThe solvent was then removed in vacuo
  4. customthe residue was purified by a flash chromatography (EtOAc:Hex=1:1.5)

Sources & evidence

ORD record
ord-cfb86b97d708488b9a3345df0037ebdc
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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