Hydrochloric Acid → 7-Ethoxynaphthalen-1-amine

HRID 1432826Notes

Reaction equation

HRID 1432826 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=2)[CH:11]=[CH:10][CH:9]=1)(C)(C)C.Cl.C(OC(C)C)(C)C>O1CCOCC1>[CH2:19]([O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][CH:9]=[C:8]2[NH2:7])=[CH:13][CH:14]=1)[CH3:20]

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 (7-ethoxy-naphthalen-1-yl)-carbamic acid t-butyl ester (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-naphthalen-1-ylamine (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-ef2d27660f8e4affbbba608af54c0cd5
Source dataset
uspto-grants-2009_11
Patent number
US07612113B2

Reaction notes

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