2-Naphthylacetonitrile → 2-(2-Naphthyl)ethyl-amine

HRID 1768556Notes

Reaction equation

HRID 1768556 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH2:21][C:22]#[N:23]>CCOCC>[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH2:21][CH2:22][NH2:23]

Participants

5

Reactant 3

HCID 820082-NaphthylacetonitrileHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 37843782-(2-Naphthyl)ethyl-amineYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Aluminum trichloride (7.6 g, 57 mmole) was added in portions to 30 mL of ether cooled to 0° C. under nitrogen. In a separate flask, lithium aluminum hydride (2.2 g, 57 mmole) was slurried in 30 mL of ether and cooled to -5° C. with an ice/acetone bath. The etherial aluminum trichloride solution was added dropwise to the LiAlH4 slurry at such a rate as to maintain a temperature of 0° C. Fifteen minutes after addition was complete, 2-naphthylacetonitrile (4.0 g, 24 mmole) in 40 mL of ether was added dropwise while maintaining a temperature of 0° C. The reaction mixture was stirred for an additional 15 minutes at 0° C. and then allowed to warm to room temperature for 1 hour. After recooling to 0° C., the reaction was quenched by careful dropwise addition of water. The mixture was diluted with ether, partitioned, and the aqueous phase was basified with 30% NH4OH solution. Extraction of the aqueous phase with ether, combination of the organic phases, drying, and concentration gave a colorless oil (2.7g, 67% yield).

Workup

  1. temperaturecooled to -5° C. with an ice/acetone bath
  2. temperatureto maintain a temperature of 0° C
  3. additionFifteen minutes after addition
  4. temperaturewhile maintaining a temperature of 0° C
  5. temperatureto warm to room temperature for 1 hour
  6. customAfter recooling to 0° C.
  7. customthe reaction was quenched by careful dropwise addition of water
  8. additionThe mixture was diluted with ether
  9. custompartitioned
  10. extractionExtraction of the aqueous phase with ether, combination of the organic phases
  11. customdrying
  12. concentrationconcentration

Sources & evidence

ORD record
ord-e5e03e74735949b4aa1dab96f8e6780d
Source dataset
uspto-grants-1995_01
Patent number
US05378708

Reaction notes

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