Ammonium formate → 4-(3-methyloxetan-3-yl)aniline

HRID 2404911Notes

Reaction equation

HRID 2404911 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1([CH3:15])[CH2:14][O:13][CH2:12]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:15][C:11]1([C:3]2[CH:4]=[CH:5][C:6]([NH2:8])=[CH:7][CH:2]=2)[CH2:14][O:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59256237HCID 59256237, compound

Product 1

HCID 594100794-(3-methyloxetan-3-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 3-(2-bromo-4-nitrophenyl)-3-methyloxetane (68 mg, 0.2499 mmol) in ethanol (5 mL) was added ammonium formate (68 mg, 1.078 mmol) followed by the addition of Pd/C (32 mg, 0.3007 mmol). The reaction mixture was refluxed for an additional 5 minutes, cooled to room temperature and filtered through a plug of celite. The solvent was evaporated to get 4-(3-methyloxetan-3-yl)aniline. 1H NMR (400 MHz, DMSO-d6) δ 6.93-6.90 (m, 2H), 6.56 (d, J=8.5 Hz, 2H), 4.70 (d, J=5.4 Hz, 2H), 4.45 (d, J=5.6 Hz, 2H), 1.55 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for an additional 5 minutes
  2. filtrationfiltered through a plug of celite
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6aafa8d0aa954a48a1c2f27f797a944a
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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