Hydrazine hydrate (1:1) → HCID 54057307, compound

HRID 442671Notes

Reaction equation

HRID 442671 reaction equation
[CH2:1]1[O:29][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=4)=[N:11][N:10]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:9](=[O:27])[CH2:8][C:7]=3[CH:28]=[C:3]2[O:2]1.O.NN>C(O)C.Cl.[Ni]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:6]3[CH:5]=[C:4]4[O:29][CH2:1][O:2][C:3]4=[CH:28][C:7]=3[CH2:8][C:9](=[O:27])[N:10]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[N:11]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54562344HCID 54562344, compound

Product 1

HCID 54057307HCID 54057307, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7,8-methylenedioxy-1-(4-nitrophenyl)-3-(3-pentyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (48 mg, 0.123 mmol) in ethanol (10 mL) was added hydrazine hydrate (0.5 mL), 3 drops of conc. HCl, and excess amount of Raney Ni and the mixture obtained was stirred at room temperature for 1.5 h. Then the Raney Ni was removed by decanting. The crude product obtained by removal of the solvent was purified by flash chromatography (1:1 of hex:EtOAc) to give the product (42 mg, 94%), 1H NMR (CDCl3) 7.46 (d, J=8.3, 2H), 6.69 (d, J=8.3, 2H), 6.85 (s, 1H), 6.70 (s, 1H), 6.04, (bs, 1H), 6.01 (bs, 1H), 4.49 (heptet, J=4.9, 1H), 3.92 (bs, 2H), 3.50 (d, J=16.3, 1H), 3.29 (d, J=16.3, 1H), 2.10 (m, 1H), 1.72 (m, 1H), 1.48 (m, 21H), 0.98 (t, J=7.2, 3H), 0.48 (t, J=7.2, 3H).

Workup

  1. customthe mixture obtained
  2. customThen the Raney Ni was removed
  3. customby decanting
  4. customThe crude product obtained by removal of the solvent
  5. customwas purified by flash chromatography (1:1 of hex:EtOAc)

Sources & evidence

ORD record
ord-ebd1bfc052e74d18b05c423bc5c35977
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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