Hydrazine hydrate (1:1) → HCID 21105722, compound

HRID 1354365Notes

Reaction equation

HRID 1354365 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[C:18]3[C:17]4[CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:16]=4[O:15][C:14]=3[C:13]([O:26][CH3:27])=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>[Ni].CO.CN(C=O)C>[C:1]1([NH:7][C:8]([C:10]2[C:18]3[C:17]4[CH:19]=[C:20]([NH2:23])[CH:21]=[CH:22][C:16]=4[O:15][C:14]=3[C:13]([O:26][CH3:27])=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21105723HCID 21105723, compound

Product 1

HCID 21105722HCID 21105722, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

N1-phenyl-4-methoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (100 mg) (from step1) was reduced using raney nickel (100 mg) in methanol (40 ml) and DMF (10 ml) in the presence of hydrazine hydrate (0.5 ml) under gentle reflux for 1 h. The reaction mixture was fliterd through celite and the filterate was concentrated in vaccuo. The residue was triturated with water, to obtain a solid which was filtered dried to give the product as white solid (90 mg).

Workup

  1. temperatureunder gentle reflux for 1 h
  2. concentrationthe filterate was concentrated in vaccuo
  3. customThe residue was triturated with water
  4. customto obtain a solid which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-2fa411bf34f9482fb2b464c4b9273562
Source dataset
uspto-grants-2007_05
Patent number
US07223789B2

Reaction notes

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