Triethylamine → N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine

HRID 448878

Reaktionsgleichung

Reaktionsgleichung von HRID 448878
[CH2:1]1[CH2:11][C:9](=O)[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.Cl.[NH2:13][OH:14].C(N(CC)CC)C>CO>[C:9]1(=[N:13][OH:14])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][CH2:11]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 107241-TetraloneHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 76876N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamineAusbeute 108,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of α-tetralone (10 g, 68.5 mmol) in anhydrous MeOH (175 mL), hydroxylamine hydrochloride (7.6 g, 109.6 mmol) and triethylamine (15.3 mL, 109.6 mmol) were added. The mixture was stirred at room temperature for 16 hrs, followed by removal of the solvent in vacuo. The residue was dissolved in DCM, washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to yield crude 3,4-dihydro-2H-naphthalen-1-one oxime (12 g). MS [M+H]+: 162.1; tR=2.03 min. (method 1)

Aufarbeitung

  1. customfollowed by removal of the solvent in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e6abb06940f34a21842540b7f830e82c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481738B2

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