Hydrazine hydrate (1:1) → HCID 54018220, compound

HRID 442672Notes

Reaction equation

HRID 442672 reaction equation
[CH2:1]1[O:30][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][N:10]([C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=4)[C:9](=[O:28])[CH2:8][C:7]=3[CH:29]=[C:3]2[O:2]1.O.NN>C(O)C.Cl.[Ni]>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([N:10]2[C:9](=[O:28])[CH2:8][C:7]3[CH:29]=[C:3]4[O:2][CH2:1][O:30][C:4]4=[CH:5][C:6]=3[C:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[N:11]2)=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54082508HCID 54082508, compound

Product 1

HCID 54018220HCID 54018220, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7,8-methylenedioxy-3-(4-nitrophenyl)-1-phenyl-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (15 mg, 0.037 mmol) in ethanol (5 mL) was added HCl (conc. 2 drops), hydrazine hydrate (0.3 mL) and Raney Ni (excess) and the reaction was stirred for 40 min. The excess Raney Ni was removed by filtration and the pure product (9 mg, 66%) was obtained by flash chromatography (12.5% acetone in CH2Cl2). 1H NMR (CDCl3) 7.60 (m, 2H), 7.42 (m, 3H), 7.20 (d, J=8.6, 2H), 6.92 (s, 1H), 6.71 (d, J=8.6, 2H), 6.68 (s, 1H), 6.07 (s, 1H), 6.03 (s, 1H), 3.80-3.45 (m, 4H).

Workup

  1. customThe excess Raney Ni was removed by filtration

Sources & evidence

ORD record
ord-b49c95fb31bf4875b212c80b1676b6b6
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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