Hydrochloric Acid → 7-Ethoxynaphthalen-1-amine

HRID 416125Notes

Reaction equation

HRID 416125 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.C(OC(C)C)(C)C>O1CCOCC1>[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 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 59731041tert-Butyl 7-ethoxynaphthalen-1-ylcarbamate

Product 1

HCID 450914037-Ethoxynaphthalen-1-amineYield 86.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Next, to a solution of tert-butyl (7-ethoxy-1-naphthyl)carbamate (47.9 g, 167 mmol) in 100 mL anhydrous 1,4-dioxane was added 4N HCl in 1,4-dioxane (100 mL) at 0° C. The mixture was stirred at room temperature for 2 hours. Diisopropyl ether was added to the reaction mixture and the precipitate was filtered. To the obtained solid was added saturated sodium bicarbonate and the product was extracted with ethylacetate. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford (7-ethoxy-1-naphthyl)amine (27.0 g, 86.3% yield).

Workup

  1. filtrationthe precipitate was filtered
  2. additionTo the obtained solid was added saturated sodium bicarbonate
  3. extractionthe product was extracted with ethylacetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df58c3f36f0d4a8fb2a6fd16218b0d8f
Source dataset
uspto-grants-2012_01
Patent number
US08088826B2

Reaction notes

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