Ammonium formate → 2-Tert-butyl-5-aminobenzonitrile

HRID 1915398Notes

Reaction equation

HRID 1915398 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:6]=1[C:7]#[N:8])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:1]([C:5]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:6]=1[C:7]#[N:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57470259HCID 57470259, compound

Product 1

HCID 574702602-Tert-butyl-5-aminobenzonitrileYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 2-tert-butyl-5-nitrobenzonitrile (816 mg, 4.0 mmol) in EtOH (20 mL) was added ammonium formate (816 mg, 12.6 mmol), followed by 10% Pd—C (570 mg). The reaction mixture was refluxed for additional 90 min, cooled to room temperature and filtered through Celite. The filtrate was concentrated to give 2-tert-butyl-5-aminobenzonitrile (E-2) (630 mg, 91%), which was used without further purification. HPLC ret. time 2.66 min, 10-99% CH3CN, 5 min run; ESI-MS 175.2 m/z (MH+).

Workup

  1. temperatureThe reaction mixture was refluxed for additional 90 min
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-79fcbcdd7f954d8c88910fcdbd0eb212
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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