Hydrazine hydrate (1:1) → HCID 21105724, compound

HRID 746441Notes

Reaction equation

HRID 746441 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1.O.NN>[Ni].CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10316625HCID 10316625, compound

Product 1

HCID 21105724HCID 21105724, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

N1-(pyrid-3-yl)-4-methoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (500 mg) (from step 1) was reduced using raney nickel (150 mg) (30% w/w aqueous suspension) in methanol (10 ml) in the presence of hydrazine hydrate (0.32 ml) under gentle reflux for 4 h. The reaction mixture was flitered 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 (300 mg).

Workup

  1. temperatureunder gentle reflux for 4 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-70ef4c0338cb4a9f9595a44339a73fa9
Source dataset
uspto-grants-2008_07
Patent number
US07393846B2

Reaction notes

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