Hydrazine hydrate (1:1) → Benzofuran-7-amine

HRID 641756Notes

Reaction equation

HRID 641756 reaction equation
O.NN.[N+:4]([C:7]1[C:15]2[O:14][CH:13]=[CH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)([O-])=O>[Ni].CO>[NH2:4][C:7]1[C:15]2[O:14][CH:13]=[CH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 112866387-Nitrobenzofuran

Product 1

HCID 11217277Benzofuran-7-amineYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

Hydrazine hydrate (0.45 ml) was added dropwise to a stirred mixture of 7-nitrobenzofuran (J. Med. Chem., 1988, 31, 1934; 0.5 g), Raney nickel (0.02 g) and methanol (9 ml) that had been warmed to 55° C. The resultant mixture was heated to reflux for 30 minutes. The catalyst was removed by filtration and the filtrate was evaporated. The residue was partitioned between methylene chloride and water. The organic phase was dried over magnesium sulphate and evaporated to give 7-aminobenzofuran (0.4 g) as an oil; NMR Spectrum: (DMSOd6) 5.25 (br s, 2H), 6.55 (d, 1H), 6.8 (m, 2H), 6.9 (t, 1H), 7.85 (d, 1H).

Workup

  1. temperatureto reflux for 30 minutes
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated
  4. customThe residue was partitioned between methylene chloride and water
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-0a8b6475a9754a9bb1a66d1e6bf89d96
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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