Hydrazine hydrate (1:1) → HCID 67186774, compound

HRID 735865Notes

Reaction equation

HRID 735865 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[O:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].O.NN>C(O)(C)C.[Ni]>[CH:12]1[C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:1][NH2:2])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67187243HCID 67187243, compound

Product 1

HCID 67186774HCID 67186774, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 4-(4-cyanophenyl) dibenzofuran (20 g, 0.074 mol) in isopropylalcohol (1.5 L) was added Raney-Nickel (10 g) with stirring. The reaction mixture was heated to reflux, treated with hydrazine hydrate (100 mL) and refluxed for 6 h. The reaction mixture was cooled, filtered through celite and washed with isopropylalcohol. The filtrate was concentrated and crude purified by column chromatography over silica gel (CHCl3/MeOH; 9:1) to give the title compound as a solid (6.5 g, 32%). 1H NMR (THF-d8, 300 MHz) δ 7.30-8.30 (m, 13H), 3.98 (s, 2H)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed for 6 h
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered through celite
  6. washwashed with isopropylalcohol
  7. concentrationThe filtrate was concentrated
  8. customcrude purified by column chromatography over silica gel (CHCl3/MeOH; 9:1)

Sources & evidence

ORD record
ord-adcc08b147e249ec9d06be566c8eb5e2
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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