Hydrazine hydrate (1:1) → HCID 9978431, compound

HRID 1293466Notes

Reaction equation

HRID 1293466 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10].O.NN>CO.[Ni]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH2:24])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9980214HCID 9980214, compound

Product 1

HCID 9978431HCID 9978431, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a suspension of N-(3,5-dichloropyrid-4-yl)-4-methoxy-8-nitro dibenzo[b,d]furan-1-carboxamide (example 38) (4.8 gm, 0.011 mol) in methanol (25 ml) was added activated raney nickel (1.44 gm, 30% w/w) and stirred at reflux for 10 min. Hydrazine hydrate (1.117 gm, 0.022 mol) was added dropwise to the above refluxing reaction mixture. The reaction was refluxed for further 30 min. and filtered through celite bed. The filterate was concentrated in vaccuo and the residue was purified using silica gel chromatography using 15% acetone in chlroform as the eluent to afford 3.5 gm of N-(3,5-dichloropyrid-4-yl)-4-methoxy-8-amino-dibenzo[b,d]furan-1-carboxamide as white solid. mp: 249° C. (dec).

Workup

  1. temperatureat reflux for 10 min
  2. temperatureabove refluxing
  3. customreaction mixture
  4. temperatureThe reaction was refluxed for further 30 min.
  5. filtrationfiltered through celite bed
  6. concentrationThe filterate was concentrated in vaccuo
  7. customthe residue was purified

Sources & evidence

ORD record
ord-e4a5df0fb97c4ff8821eb6924d8aea19
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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