Aniline → (7-Methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile

HRID 1454019Notes

Reaction equation

HRID 1454019 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=O)=[CH:5][CH:4]=1.[C:14]([CH2:16]C(O)=O)#[N:15].C(O)(=O)CCCCCC.NC1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[CH2:16][C:14]#[N:15])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8094Heptanoic AcidHCID 9740Cyanoacetic acidHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 11287102(7-Methoxy-3,4-dihydronaphthalen-1-yl)acetonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

There are introduced into a 670 litre reactor 85.0 kg of 7-methoxy-1-tetralone, 60.3 kg of cyanoacetic acid and 15.6 kg of heptanoic acid in toluene in the presence of 11.0 kg of aniline. The mixture is heated at reflux. When all the starting substrate has disappeared, the solution is cooled and filtered. The precipitate obtained is washed with toluene and then the filtrate obtained is washed with a 2N sodium hydroxide solution, and subsequently with water until neutral. After removal of the solvent by evaporation, the resulting solid is recrystallised from an ethanol/water (80/20) mixture to give the title product in a yield of 87% and with a chemical purity exceeding 99%.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. temperaturethe solution is cooled
  4. filtrationfiltered
  5. customThe precipitate obtained
  6. washis washed with toluene
  7. customthe filtrate obtained
  8. washis washed with a 2N sodium hydroxide solution
  9. customAfter removal of the solvent
  10. customby evaporation
  11. customthe resulting solid is recrystallised from an ethanol/water (80/20) mixture

Sources & evidence

ORD record
ord-f213a397b9d84fd3a80a77b84806f208
Source dataset
uspto-grants-2009_01
Patent number
US07476751B2

Reaction notes

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