7-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline → 1-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

HRID 494173

Reaktionsgleichung

Reaktionsgleichung von HRID 494173
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])=[CH:6][CH:5]=1

Komponenten

4

Edukt 1

HCID 125783617-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 820484221-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanoneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D4) (1.51 g, 5.5 mmol) and 10% palladium on charcoal (150 mg, 54% water) in methanol (80 ml) was hydrogenated at atmospheric pressure and ambient temperature for 24 h. The catalyst was removed by filtration and was washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the title compound as a pale orange solid (1.29 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.05 (br, 1H), 6.95 (d, 1H), 6.54 (dd, 1H), 3.78 (m, 2H), 3.65 (br, 2H), 2.74 (br, 2H), 2.03 (m, 2H).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. washwas washed with further methanol
  3. filtrationThe combined filtrated
  4. concentrationwashings were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3f558095e0f045e4a530bc8a8a7e2b1f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538121B2

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