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

HRID 30531

Reaction equation

HRID 30531 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.C(=O)(O)[O-].[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 516892Sodium BicarbonateHCID 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-ylamine (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 bicarbonate, and the product was extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 8-amino-3,4-dihydro-1H-naphthalen-2-one (0.71 g, 78% yield).

Workup

  1. extractionthe product was extracted with ethyl acetate
  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-61ab543b339a4ddfa2409d1072f93553
Source dataset
uspto-grants-2008_09
Patent number
US07423175B2

Linked notes

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