2-Methyl-2-(4-nitrophenyl)propan-1-ol → 2-(4-Aminophenyl)-2-methylpropan-1-ol

HRID 2364871Notes

Reaction equation

HRID 2364871 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4]>C1COCC1.C(O)C.[Pt](=O)=O>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:2]([CH3:5])([CH3:1])[CH2:3][OH:4])=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 222492792-Methyl-2-(4-nitrophenyl)propan-1-ol

Product 1

HCID 219047282-(4-Aminophenyl)-2-methylpropan-1-olYield 134.2%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 194B (0.321 g, 1.644 mmole) was dissolved in a mixture of THF (10 mL) and ethanol (2 mL). To this was added platinum(IV) oxide (0.030 g, 0.131 mmole). The flask was capped with a septum and the contents vacuum degassed three times. Hydrogen was introduced via a balloon and the mixture stirred at room temperature. An additional 38.2 mg (0.167 mmole) of catalyst was added in two aliquots before chromatographic analysis indicated that the starting material was consumed. After stirring overnight under hydrogen the mixture was filtered through a sand/celite plug followed by an ethyl acetate rinse. The filtrate was concentrated to dryness and the residue purified by chromatography on amine modified silica gel eluting with ethyl acetate—hexane beginning at 8% and advancing to 66% ethyl acetate to provide the title compound (0.3645 g, 68% yield) as a clear oil. MS (DCI+) m/z @ 183.1 (M+NH4)+.

Workup

  1. customThe flask was capped with a septum
  2. customthe contents vacuum degassed three times
  3. additionHydrogen was introduced via a balloon
  4. customwas consumed
  5. stirringAfter stirring overnight under hydrogen the mixture
  6. filtrationwas filtered through a sand/celite plug
  7. washrinse
  8. concentrationThe filtrate was concentrated to dryness
  9. customthe residue purified by chromatography on amine

Sources & evidence

ORD record
ord-93c04934576149f984e38a10ac07bbd2
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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