Triethylamine → 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one Oxime

HRID 32109Notes

Reaction equation

HRID 32109 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[CH2:11][CH2:10][CH2:9]2.Cl.[NH2:19][OH:20].CCN(CC)CC>CO.CCOC(C)=O>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[N:19][OH:20])[CH2:11][CH2:10][CH2:9]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 122143876-(2-Dimethylaminoethoxy)-1-tetralone

Product 1

HCID 724406286-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one Oxime

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.53 g, 2.3 mmol), hydroxylamine hydrochloride (Riedel DeHaen, 0.69 g, 10.0 mmol), and Et3N (Aldrich, 1.4 mL, 10.0 mmol) in MeOH (6 mL) was heated to reflux overnight. The reaction mixture was diluted with EtOAc (70 mL) and washed with 10% Na2CO3, brine. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo to afford the product as an off-white solid. MS (ESI): 249 (M+H)+.

Workup

  1. temperatureto reflux overnight
  2. washwashed with 10% Na2CO3, brine
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea227f3f465f4bc0a9880d52e033bbaf
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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