Water → 1-{6-[Ethyl-(2-hydroxylethyl)-amino]-2-naphthyl}ethanone

HRID 1391987Notes

Reaction equation

HRID 1391987 reaction equation
O[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2.[CH2:15]([NH:17][CH2:18][CH2:19][OH:20])[CH3:16].O>C(OCC)(=O)C>[CH2:15]([N:17]([CH2:18][CH2:19][OH:20])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2)[CH3:16]

Participants

5

Reactant 3

HCID 962Water2×HCID 80722-(Ethylamino)ethanolHCID 826311-(6-Hydroxy-2-naphthyl)ethan-1-one

Product 1

HCID 153748091-{6-[Ethyl-(2-hydroxylethyl)-amino]-2-naphthyl}ethanoneYield 12%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(6-hydroxy-2-naphthyl)ethanone (744 mg, 3.92 mmol), sodium hydrogen sulfate(IV) (1.66 g, 16 mmol), 2-ethylaminoethanol (2 mL) and water (5 mL) was heated in a steel bomb at 130-140° C. for 3 days. After cooling, the mixture was distributed between water and ethyl acetate, and the organic layer was washed with brine, dried and evaporated. The residue was dissolved in acetone and loaded onto a 4 mm dry silica plate for radial chromatography. The plate was eluted with a 1:1 mixture of petroleum ether and ethyl acetate. Appropriate fractions were collected and evaporated to give 125 mg (12%) of 1-{6-[ethyl-(2-hydroxylethyl)-amino]-2-naphthyl}ethanone.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed with brine
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in acetone
  6. washThe plate was eluted with a 1:1 mixture of petroleum ether and ethyl acetate
  7. customAppropriate fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-a10e9a933d8b4aa0bb86ad30ab944872
Source dataset
uspto-grants-2008_03
Patent number
US07341709B2

Reaction notes

Loading…