Ethanol → HCID 68673467, compound

HRID 1927663Notes

Reaction equation

HRID 1927663 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-])=O.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 68674457HCID 68674457, compound

Product 1

HCID 68673467HCID 68673467, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-nitro-2-pyridin-2-ylbenzonitrile (370 mg, 1.69 mmol), iron powder (473 mg, 8.45 mmol), ammonium chloride (99 mg, 1.86 mmol), ethanol (20 mL) and water (10 mL) was heated at reflux for 1 h. Upon cooling, the reaction mixture was filtered through Celite, rinsed with ethyl acetate, and the filtrate was concentrated. The resulting residue was purified by flash column chromatography on silica gel eluting with 0-50% ethyl acetate hexanes to provide 5-amino-2-pyridin-2-ylbenzonitrile.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperatureUpon cooling
  4. filtrationthe reaction mixture was filtered through Celite
  5. washrinsed with ethyl acetate
  6. concentrationthe filtrate was concentrated
  7. customThe resulting residue was purified by flash column chromatography on silica gel eluting with 0-50% ethyl acetate hexanes

Sources & evidence

ORD record
ord-4d094e3fe25f4153a7dd70b69fd7a3b6
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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