2-Methyl-1-[(2-methyl-2-propanyl)oxy]-3-nitrobenzene → 3-(Tert-butoxy)-2-methylaniline

HRID 731517Notes

Reaction equation

HRID 731517 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:13]([O-])=O>C(O)C.[Pd]>[CH3:1][C:2]1[C:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:13]

Participants

4

Reactant 1

HCID 450971602-Methyl-1-[(2-methyl-2-propanyl)oxy]-3-nitrobenzene

Product 1

HCID 578366553-(Tert-butoxy)-2-methylanilineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-3-tert-butoxynitrobenzene K3 (1.31 g; 6.26 mmol) in absolute ethanol (30 mL) was added 10% Pd/C catalyst (130 mg). The solution was hydrogenated under a hydrogen filled balloon at atmospheric pressure and room temperature for 63 h. The reaction mixture was filtered through a Celite pad, rinsed with absolute EtOH and evaporated to dryness to provide 2-methyl-3-tert-butoxyaniline K4 (1.1 g; 6.14 mmol; 98% yield). M.S. 180 (M+H)+. Homogeneity by HPLC (TFA) @220 nm: 96%

Workup

  1. customat atmospheric pressure and room temperature
  2. customfor 63 h
  3. filtrationThe reaction mixture was filtered through a Celite pad
  4. washrinsed with absolute EtOH
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-24db9ea53e1b4d8e9ad4b51bda7e697d
Source dataset
uspto-grants-2009_09
Patent number
US07585845B2

Reaction notes

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