Hydrochloric Acid → HCID 10040148, compound

HRID 442688Notes

Reaction equation

HRID 442688 reaction equation
[CH2:1]1[O:24][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[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:15]1[CH:14]=[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:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 10592117HCID 10592117, compound

Product 1

HCID 10040148HCID 10040148, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 7,8-methylenedioxy-1-(3-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (20 mg, 0.061 mmol) in ethanol (5 ml,) was added Raney Ni (54 mg), hydrazine hydrate (40 μL, 0.71 mmol), and 2N HCl (60 μL, 0.12 mmol). The mixture was stirred at room temperature for 24 h. The solid Ni was filtered out. The filtrate was concentrated in vacuo and the resulting residue was purified by chromatography (10:1 CHCl3 /EtOH) to afford the title compound as a tan solid (6 mg, 33%), mp: 118°-122° C. 1H NMR (CDCl3) 8.33 (s, 1H), 7.22-7.17 (m, 1H), 6.94 (s, 1H), 6.94-6.88 (m, 1H), 6.81 (s, 1H), 6.79-6.75 (m, 1H), 6.67 (s, 1H), 6.03 (s, 2H), 3.74 (brs, 2H), 3.44 (s, 2H).

Workup

  1. filtrationThe solid Ni was filtered out
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by chromatography (10:1 CHCl3 /EtOH)

Sources & evidence

ORD record
ord-5d29176960724f01ad6cf73d7d7cc04b
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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