Hydrochloric Acid → 7-Ethoxynaphthalen-1-amine

HRID 600770Notes

Reaction equation

HRID 600770 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[NH:14]C(=O)OC(C)(C)C)=[CH:6][CH:5]=1)[CH3:2].Cl>O1CCOCC1.C(OCC)C>[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]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59731041tert-Butyl 7-ethoxynaphthalen-1-ylcarbamate

Product 1

HCID 450914037-Ethoxynaphthalen-1-amineYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of the product of Example 1C (14.47 g, 50.4 mmol) in dioxane (30 mL) at 0° C. was added 4N HCl in dioxane (60 mL, 240 mmol). The reaction mixture was stirred at room temperature for 3.5 hours, diluted with 3 volumes of diethyl ether. The resulting dark brown precipitate was collected by filtration. It was then treated with saturated NaHCO3 solution and was extracted with ethyl acetate. The solution was dried over MgSO4, filtered and evaporated in vacuo to yield the title compound (4.88 g, 52%).

Workup

  1. filtrationThe resulting dark brown precipitate was collected by filtration
  2. additionIt was then treated with saturated NaHCO3 solution
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8d3583298bfc4a8f9fcd982086892242
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Reaction notes

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