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

HRID 30530

Reaction equation

HRID 30530 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 flask containing a mixture of 7-ethoxy-naphthalen-1-ylamine (1.80 g, 9.61 mmol) and t-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-ylamine (1.37 g, 76% yield).

Workup

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

Sources & evidence

ORD record
ord-e8fa031bb0b149fca7ae542ca3797309
Source dataset
uspto-grants-2008_09
Patent number
US07423175B2

Linked notes

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