Ammonium Chloride → 2-phenyl-1H-indol-6-amine

HRID 1886958Notes

Reaction equation

HRID 1886958 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:13]1([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=3)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 207598016-Nitro-2-phenyl-1H-indole

Product 1

HCID 114131282-phenyl-1H-indol-6-amineYield 35.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
70 °C

Procedure

6-Nitro-2-phenyl-1H-indole (175 mg, 0.73 mmol), ammonium chloride (80 mg, 1.47 mmol) and iron powder (205 mg, 3.68 mmol) were suspended in ethanol/water (4 mL/2 mL) and heated at 70° C. for 2 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 purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 10:90 v/v to ethyl acetate/hexanes 50:50 v/v) to afford 54 mg (35%) 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. customwas purified by column chromatography
  7. washeluting

Sources & evidence

ORD record
ord-c8634ff753e048cba37262e287e69371
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

Loading…