Hydrochloric Acid → 7-Ethoxynaphthalen-1-amine

HRID 130636Notes

Reaction equation

HRID 130636 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-fd94424db17f4589bc77dc3a3ac40654
Source dataset
uspto-grants-2008_06
Patent number
US07381840B2

Reaction notes

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