Hydrochloric Acid → HCID 9839097, compound

HRID 442669Notes

Reaction equation

HRID 442669 reaction equation
[CH2:1]1[O:24][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][NH:10][C:9](=[O:22])[CH2:8][C:7]=3[CH:23]=[C:3]2[O:2]1.O.NN.Cl>C(O)C.[Ni]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[C:6]3[CH:5]=[C:4]4[O:24][CH2:1][O:2][C:3]4=[CH:23][C:7]=3[CH2:8][C:9](=[O:22])[NH:10][N:11]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 10829879HCID 10829879, compound

Product 1

HCID 9839097HCID 9839097, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 7,8-methylenedioxy-1-(4-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (167 mg, 0.51 mmol) in ethanol (8 mL) was added Raney Ni (430 mg), hydrazine hydrate (200 μL, 3.5 mmol) and 2N HCl (150 μL, 0.3 mmol). The mixture was stirred at room temperature for 17 h. The solid Ni was filtered out. The filtrate was concentrated in vacuo and the resulting residue was separated by chromatography (1:4 hexane/EtOAc) to afford the title compound as a yellow solid (110 mg, 0.37 mmol, 73%), mp: 242°-244° C. 1H NMR (CDCl3) 8.32 (s, 1H), 7.41 (d, 2H, J=8.5), 6.81 (s, 1H), 6.70 (s, 1H), 6.68 (d, 2H, J=8.5), 6.02 (s, 2H), 3.94 (brs, 2H), 3.42 (s, 2H). Anal. Calcd. for C16H13N3O3.0.25H2O: C, 64.10; H, 4.54; N, 14.02. Found C, 64.32; H, 4.37; N, 13.48.

Workup

  1. filtrationThe solid Ni was filtered out
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was separated by chromatography (1:4 hexane/EtOAc)

Sources & evidence

ORD record
ord-45442c3b60da4c3d8dad49574172205d
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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