Ethanol → 4-(5-Amino-1-benzofuran-7-yl)pyridine

HRID 1161984Notes

Reaction equation

HRID 1161984 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O.C(O)C.O.NN>O1CCOCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 66893958HCID 66893958, compound2×

Product 1

HCID 668930874-(5-Amino-1-benzofuran-7-yl)pyridine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

4-(5-Nitro-1-benzofuran-7-yl)pyridine (125 mg, 0.520 mmol; Intermediate 11) was dissolved in 1,4-dioxane (15 mL). After addition of ethanol (20 mL), Raney-nickel (slurry in ethanol; 2 mL) and hydrazine hydrate (4 mL) were added and the mixture was left stirring at room temperature overnight. The product was used directly in the subsequent reaction after filtration through Celite and evaporation of solvent.

Workup

  1. additionwere added
  2. waitthe mixture was left
  3. customThe product was used directly in the subsequent reaction
  4. filtrationafter filtration
  5. customthrough Celite and evaporation of solvent

Sources & evidence

ORD record
ord-f1e37edef826442c9d9c704dbfd9df1c
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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