Trifluoroacetic acid → HCID 68755585, Verbindung

HRID 1519745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519745
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([CH2:13][C:14]([OH:16])=[O:15])=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 687591091,1-Dimethylethyl 8-(trifluoromethyl)-5-quinolineacetate

Produkt 1

HCID 68755585HCID 68755585, VerbindungAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-(8-(trifluoromethyl)quinolin-5-yl)acetate (400 mg, 1.28 mmol) in DCM (5 mL) was added TFA (10 mL) dropwise. The reaction was stirred at room temperature overnight. After the reaction was complete, the solvent was removed and the residue was purified (silica gel chromatography) to give the final product 2-(8-(trifluoromethyl)quinolin-5-yl)acetic acid (180 mg, 54%). LC-MS (0.05% TFA): [M+1]+ 256.1. 1H-NMR (DMSO-d6, 400 MHz): δ 12.70 (s, 1H), 9.07(m, 1H), 8.56 (m, 1H), 8.15 (d, 1H), 7.74(m,1H), 7.68 (m,1H), 4.23(s, 2H). 13C-NMR (DMSO-d6, 100MHz): 67 171.9, 151.0, 144.0, 138.3, 133.5, 127.87, 127.83, 127.78, 125.3, 123.1, 122.2, 37.7.

Aufarbeitung

  1. customthe solvent was removed
  2. customthe residue was purified (silica gel chromatography)

Quellen und Nachweise

ORD-Eintrag
ord-0885c9adea1942809ef3086bd5d37601
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073891B2

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