Potassium Formate → 4-(tert-Butyl)-3-methoxyaniline

HRID 423796Notes

Reaction equation

HRID 423796 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[K+]>CCO.O.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2735122Potassium FormateHCID 574702101-Tert-butyl-2-methoxy-4-nitrobenzene

Product 1

HCID 574701524-(tert-Butyl)-3-methoxyanilineYield 72.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a refluxing solution of 1-tert-butyl-2-methoxy-4-nitrobenzene (82 mg, 0.4 mmol) in EtOH (2 mL) was added potassium formate (300 mg, 3.6 mmol) in water (1 mL), followed by 10% Pd—C (15 mg). The reaction mixture was refluxed for additional 60 min, cooled to room temperature and filtered through Celite. The filtrate was concentrated to dryness to give 4-tert-butyl-3-methoxyaniline (C-2) (52 mg, 72%) that was used without further purification. HPLC ret. time 2.29 min, 10-99% CH3CN, 5 min run; ESI-MS 180.0 m/z (MH+).

Workup

  1. temperatureThe reaction mixture was refluxed for additional 60 min
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a11e7efe97f0412aa0fcce6bc98bec70
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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