Hydrazine hydrate (1:1) → HCID 21105718, compound

HRID 131600Notes

Reaction equation

HRID 131600 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[C:20]3[C:19]4[CH:21]=[C:22]([N+:25]([O-])=O)[CH:23]=[CH:24][C:18]=4[O:17][C:16]=3[C:15]([O:28][CH3:29])=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1.O.NN>[Ni].CO.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[C:20]3[C:19]4[CH:21]=[C:22]([NH2:25])[CH:23]=[CH:24][C:18]=4[O:17][C:16]=3[C:15]([O:28][CH3:29])=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21105719HCID 21105719, compound

Product 1

HCID 21105718HCID 21105718, compoundYield 69.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

N1-(4-methoxyphenyl)-4-methoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (140 mg) (from step 1) was reduced using raney nickel (100 mg) in methanol (40 ml) and DMF (10 ml) in the presence of hydrazine hydrate (1.0 ml) under gentle reflux for 1 h. The reaction mixture was filtered 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. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filterate was concentrated in vaccuo
  4. customThe residue was triturated with water
  5. customto obtain a solid which
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-65b01cd5eb0c45e7b8120dc3ffcec4bd
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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