Hydrochloric Acid → 8-Amino-3,4-dihydro-1H-naphthalen-2-one

HRID 416127

Reaction equation

HRID 416127 reaction equation
C([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)C.Cl.[Na]>O1CCCC1>[NH2:14][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][C:4](=[O:3])[CH2:5][CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 230669967-Ethoxy-5,8-dihydronaphthalen-1-amine

Product 1

HCID 230669938-Amino-3,4-dihydro-1H-naphthalen-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (7-ethoxy-5,8-dihydronaphthalen-1-yl)amine (1.07 g, 5.65 mmol) in tetrahydrofuran (30 mL) was added solution of aqueous 2N HCl (10 mL), and stiired at 40° C. for 1 hour. The mixture was neutralized with addition of sodium bicorbonate, and the product was extracted with ethylacetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 8-amino-3,4-dihydronaphthalen-2(1H)-one (0.71 g, 78% yield).

Workup

  1. extractionthe product was extracted with ethylacetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5194317c5534c8eaa8ca22f586c5afe
Source dataset
uspto-grants-2012_01
Patent number
US08088826B2

Linked notes

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