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

HRID 1984761Notes

Reaction equation

HRID 1984761 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

Conditions

Temperature
40 °C

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 stirred 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-0bf810c97afa4464932612249490f313
Source dataset
uspto-grants-2009_06
Patent number
US07544716B2

Reaction notes

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