Ammonia → 7-Ethoxy-5,8-dihydronaphthalen-1-amine

HRID 1434545Notes

Reaction equation

HRID 1434545 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[NH2:14])=[CH:6][CH:5]=1)[CH3:2].C(O)(C)(C)C.[Li].N>O1CCCC1.O.CO>[CH2:1]([O:3][C:4]1[CH2:13][C:12]2[C:11]([NH2:14])=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]=1)[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6386tert-ButanolHCID 3028194LithiumHCID 450914037-Ethoxynaphthalen-1-amine

Product 1

HCID 230669967-Ethoxy-5,8-dihydronaphthalen-1-amineYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Next, to a mixture of (7-ethoxy-1-naphthyl)amine (1.80 g, 9.61 mmol) and tert-butanol (2.13 g, 28.8 mmol) in tetrahydrofuran (20 mL) was collected liquid ammonia (300 mL) at −78° C. To the mixture was added lithium (0.200 g, 28.8 mmol) over 30 minutes and stirred at −78° C. for 1 hour. Methanol and water was added, and the mixture was stirred at room temperature for 16 hours to allow ammonia to evaporate. To the obtained residue was added ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford (7-ethoxy-5,8-dihydronaphthalen-1-yl)amine (1.37 g, 76% yield).

Workup

  1. customwas collected liquid ammonia (300 mL) at −78° C
  2. stirringthe mixture was stirred at room temperature for 16 hours
  3. customto evaporate
  4. additionTo the obtained residue was added ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac725cbdbf7b4fd89a8324d1ea422464
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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