Trifluoroacetic acid → [2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-3,4-dihydro-2H-naphthalen-1-ylidene)amine

HRID 914991

Reaktionsgleichung

Reaktionsgleichung von HRID 914991
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][NH2:13].[N+:14]([C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][CH2:23][C:24]2=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][N:13]=[C:24]1[C:25]2[C:20](=[CH:19][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:26]=2)[CH2:21][CH2:22][CH2:23]1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 384457-Nitro-1-tetraloneHCID 407422-(1,2,3,4-Tetrahydroisoquinolin-2-yl)ethan-1-amine

Produkt 1

HCID 58958206[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-3,4-dihydro-2H-naphthalen-1-ylidene)amineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 36 (964 mg, 5.48 mmol) and 7-nitro-3,4-dihydro-2H-naphthalen-1-one (95) (1.05 g, 5.48 mmol) in toluene (30 mL) was added a catalytic amount of TFA. The reaction was heated at 130° C. overnight before it was allowed to cool to room temperature and diluted with EtOAc (100 mL). The organic solution was sequentially washed with saturated NaHCO3 (aq. 100 mL), brine (100 mL), dried over Na2SO4, and concentrated to give 96 as a brown oil (1.8 g, 94%).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washThe organic solution was sequentially washed with saturated NaHCO3 (aq. 100 mL), brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-875f97cde2c04a11a6c7244706e0814f
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265122B2

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