HCID 10910721, compound → 1-Propanone, 1-(2-aminophenyl)-2,2-dimethyl-

HRID 2399685Notes

Reaction equation

HRID 2399685 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])([O-])=O>C(O)C.[Pd].Cl>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:15])[C:11]([CH3:13])([CH3:12])[CH3:14]

Participants

5

Reactant 1

HCID 10910721HCID 10910721, compound

Product 1

HCID 5775641-Propanone, 1-(2-aminophenyl)-2,2-dimethyl-Yield 70.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 1-(2-nitrophenyl)-2,2-dimethylpropan-1-one (5 g, 24 mmol) (ref: Aus. J. Chem., 34, 1875-8 (1981)) in ethanol (100 ml) was added 10% palladium on carbon (0.5 g, 10% (w/w)) in hydrochloric acid (5 ml of a 5M solution). The mixture was hydrogenated at 25 psi for 20 min, then the catalyst was filtered off and washed with methanol. The solvents were evaporated in vacuo. The oily residue was partitioned between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (50 ml). The organic phase was separated, washed with brine (25 ml), dried (Na2SO4) and evaporated. Trituration of the solid with diethyl ether afforded the title compound as a colourless solid (3 g, 70%). 1H NMR (250 MHz, CDCl3) δ 1.38 (9H, s), 5.64 (2H, brs), 6.60-7.30 (4H, m).

Workup

  1. filtrationthe catalyst was filtered off
  2. washwashed with methanol
  3. customThe solvents were evaporated in vacuo
  4. customThe oily residue was partitioned between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (50 ml)
  5. customThe organic phase was separated
  6. washwashed with brine (25 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-6b56f6a772984ffe8e26e0479350abcc
Source dataset
uspto-grants-1995_09
Patent number
US05451582

Reaction notes

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