Acetophenone → (E)-N-[(4-nitrophenyl)methoxy]-1-phenylethanimine

HRID 41927

Reaktionsgleichung

Reaktionsgleichung von HRID 41927
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([CH2:18][O:19][NH2:20])=[CH:16][CH:15]=1)([O-:13])=[O:12]>>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19]/[N:20]=[C:1](/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)\[CH3:2])=[CH:21][CH:22]=1)([O-:13])=[O:12]

Komponenten

3

Edukt 2

HCID 7410AcetophenoneHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)

Produkt 1

HCID 25100092(E)-N-[(4-nitrophenyl)methoxy]-1-phenylethanimineAusbeute 77 %

Versuchsvorschrift

Acetophenone (20) (150 mg, 1.25 mmol) was condensed with compound 19 (280 mg, 1.37 mmol) according to the general procedure II-A defined above. After heating the reaction mixture for 2 h it was cooled and the solvent removed under reduced pressure. The resulting solid was filtered off and washed with cold isopropanol (3.0 mL) to afford the title compound CP30252 (258 mg, 77%) as a pale-yellow solid, m.p. 91.3-92.3° C.

Aufarbeitung

  1. temperatureAfter heating the reaction mixture for 2 h it
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. filtrationThe resulting solid was filtered off
  5. washwashed with cold isopropanol (3.0 mL)

Quellen und Nachweise

ORD-Eintrag
ord-23a916c9fb6443c8ab25be0c5e823b60
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536157B2

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