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

HRID 22768Notes

Reaction equation

HRID 22768 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-2418f709c5754a30a206eaf6238017a7
Source dataset
uspto-grants-2005_02
Patent number
US06849625B2

Reaction notes

Loading…