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

HRID 131604Notes

Reaction equation

HRID 131604 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 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 (300 mg).

Workup

  1. temperatureunder gentle reflux for 4 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-12d673f141474b558f740bd9bcdd2cf3
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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