HCID 14997006, compound → HCID 20525448, compound

HRID 1702520Notes

Reaction equation

HRID 1702520 reaction equation
[CH3:1][O:2][CH:3]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])[CH3:4].[H][H]>[Pt].C(C(C)=O)C>[CH:3]([NH:8][C:7]1[CH:9]=[CH:10][CH:11]=[C:5]([CH:3]([O:2][CH3:1])[CH3:4])[CH:6]=1)([CH2:5][CH3:11])[CH3:4]

Participants

5

Reactant 2

HCID 14997006HCID 14997006, compound2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 20525448HCID 20525448, compoundYield 572.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
95 °C

Procedure

A 300-cubic centimeter capacity stirred autoclave equipped with a heating mantle and sample port was charged with 3.02 grams (0.02 mole) of the 3-(1-methoxyeth-1-yl)aniline prepared in paragraph (b) of Example IV and 0.6 gram of 5 percent platinum on carbon hydrogenation catalyst in 200 milliliters of methyl ethyl ketone. The autoclave was then sealed, the air driven stirrer turned on, and the temperature was brought up to and maintained at about 95° C. The autoclave was then charged with hydrogen gas to a pressure of 200 psi (the valve to the hydrogen cylinder being left open). After 5 hours' reaction, the autoclave was cooled, broken open, and the contents were removed and filtered. The filtrate was concentrated on a rotary evaporator at 55° C., leaving 11.87 grams of a light yellow liquid identified by NMR spectroscopy as N-sec-butyl-N-3-(1-methyleth-1-yl)aniline.

Workup

  1. customequipped with a heating mantle and sample port
  2. customThe autoclave was then sealed
  3. waitcylinder being left open)
  4. customAfter 5 hours' reaction
  5. temperaturethe autoclave was cooled
  6. customthe contents were removed
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated on a rotary evaporator at 55° C.

Sources & evidence

ORD record
ord-138b7388ac494c26859e8aea7d00d533
Source dataset
uspto-grants-1982_09
Patent number
US04348223

Reaction notes

Loading…