Sodium Carbonate → N-(5,6-Dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-O-ethyl-hydroxylamine

HRID 2358473Notes

Reaction equation

HRID 2358473 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH2:8]2.Cl.[CH2:17]([O:19][NH2:20])[CH3:18].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([NH:20][O:19][CH2:17][CH3:18])[CH2:8]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 76850O-ethylhydroxylamine hydrochlorideHCID 46107525,6-dimethoxy-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 11218938N-(5,6-Dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-O-ethyl-hydroxylamineYield 45.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

5,6-Dimethoxy-3,4-dihydro-1H-naphthalen-2-one (1.5 g, 7.5 mmol), prepared as described in J Med. Chem. 1977, 20, 1111-1116, was dissolved in water (15 ml) and a solution of O-ethylhydroxylamine hydrochloride (1 g, 10 mmol) and Na2CO3 (0.53 g, 5 mmol) in water (10 ml) was added dropwise under stirring at 10° C. The reaction was left at room temperature overnight and then extracted with diethyl ether. The ether solution was evaporated to dryness under vacuum. The residue was dissolved in 20 ml of ethanol and concentrated hydrochloric acid (1 ml) and hydrogenated at 3,6×106 Pa (50 psi) using PtO2 as catalyst. The solvent was removed under reduced pressure, water was added and the aqueous phase was treated with NaHCO3 and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated to dryness under vacuum. The crude residue was purified by chromatography, to afford 0.85 g of the title compound.

Workup

  1. extractionextracted with diethyl ether
  2. customThe ether solution was evaporated to dryness under vacuum
  3. dissolutionThe residue was dissolved in 20 ml of ethanol
  4. customThe solvent was removed under reduced pressure, water
  5. additionwas added
  6. additionthe aqueous phase was treated with NaHCO3
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under vacuum
  11. customThe crude residue was purified by chromatography

Sources & evidence

ORD record
ord-83347ca327944445b6616c14582a3364
Source dataset
uspto-grants-2010_07
Patent number
US07763751B2

Reaction notes

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