Ammonium Chloride → 2-Phenyl-1-benzofuran-5-amine

HRID 1886961Notes

Reaction equation

HRID 1886961 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][C:8]=2[CH:18]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.C(OCC)(=O)C.[Fe]>[C:12]1([C:10]2[O:11][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:18][C:8]=3[CH:9]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 111724805-Nitro-2-phenylbenzofuran

Product 1

HCID 167651722-Phenyl-1-benzofuran-5-amineYield 97%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To 5-Nitro-2-phenylbenzofuran (250 mg, 1.04 mmol) in ethanol/water 2:1 v/v (12 mL) at 80° C. was added ammonium chloride (112 mg, 2.09 mmol) and iron powder (292 mg, 5.23 mmol). The resulting mixture was heated at 80° C. for 4 h. After cooling, the solution was filtrated through a pad of Celite®, which was washed with ethanol. The organic layer was evaporated into vacuo to obtain a solid, which was then taken up in ethyl acetate and washed with water. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 211 mg (96%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solution was filtrated through a pad of Celite®, which
  3. washwas washed with ethanol
  4. customThe organic layer was evaporated into vacuo
  5. customto obtain a solid, which
  6. washwashed with water
  7. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-1083284d0f634c1caf50e6ff41ca2982
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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