Ammonium formate → 2-(4-Aminophenyl)-2-methylpropane-1,3-diol

HRID 2404912Notes

Reaction equation

HRID 2404912 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]([CH3:16])([CH2:14][OH:15])[CH2:12][OH:13].C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:11]([CH3:16])([CH2:14][OH:15])[CH2:12][OH:13])=[CH:2][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 592061202-(2-Bromo-4-nitrophenyl)-2-methylpropane-1,3-diol

Product 1

HCID 594100922-(4-Aminophenyl)-2-methylpropane-1,3-diolYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of 2-(2-bromo-4-nitrophenyl)-2-methylpropane-1,3-diol (211 mg, 0.73 mmol) in ethanol (15.5 mL) was added ammonium formate (211 mg, 3.35 mmol) followed by the addition of Pd/C (140 mg, 1.32 mmol). The reaction mixture was refluxed for an additional 10 minutes, cooled to room temperature and filtered through a plug of celite. The solvent was evaporated under reduced pressure to give 2-(4-aminophenyl)-2-methylpropane-1,3-diol (112 mg, 85%).

Workup

  1. temperatureThe reaction mixture was refluxed for an additional 10 minutes
  2. filtrationfiltered through a plug of celite
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2038471329e04527a5e6420338cf29aa
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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