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

HRID 2193966Notes

Reaction equation

HRID 2193966 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.C(N)C1C=CC=CC=1.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

7

Reactant 5

HCID 6115AnilineHCID 7504BenzylamineHCID 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 90%

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 12.7 kg of benzylamine (or 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 2N sodium hydroxide solution and then with water until neutrality. After evaporating off the solvent, the solid obtained is recrystallised from an ethanol/water (80/20) mixture to yield the title product in a yield of 90% and with a chemical purity of more than 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 2N sodium hydroxide solution
  9. customAfter evaporating off the solvent
  10. customthe solid obtained
  11. customis recrystallised from an ethanol/water (80/20) mixture

Sources & evidence

ORD record
ord-8fb5d1ef004d4040a7b2eeb46b828cfb
Source dataset
uspto-grants-2012_12
Patent number
US08329947B2

Reaction notes

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