Ethyl Acetate → 1-(2-Naphthyl)methanamine

HRID 1020747Notes

Reaction equation

HRID 1020747 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH2:13])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH2:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 75245Naphthalene-2-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1372821-(2-Naphthyl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Naphthalene-2-carboxylic acid amide (0.8 g, 1 eq, 4.678 mmol) was dissolved in THF (80 mL) and the solution was cooled down to 0-5° C. A 1.0 M solution of Lithium Aluminium Hydride (LAH) in THF (1.42 g, 8.0 eq, 37.0 mmol) was added drop-wise at 0-5° C. The reaction mixture was stirred at RT overnight. After completion of the reaction (confirmed by TLC), ethyl acetate at 0-5° C. was slowly added to quench the excess LAH in reaction mixture followed by the addition of saturated sodium sulphate solution (2 mL). The reaction mass was filtered through a hy-flow bed and the filtrate was concentrated in vacuo to afford the crude product.

Workup

  1. additionwas slowly added
  2. customto quench the excess LAH
  3. customin reaction mixture
  4. filtrationThe reaction mass was filtered through a hy-flow bed
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-891fd709a4d848c098b57d7745b298bb
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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