Heptane → HCID 178524447, Verbindung

HRID 478653

Reaktionsgleichung

Reaktionsgleichung von HRID 478653
C(O[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.[NH:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[NH2:18].CCCCCCC>C(O)CCC>[O:5]=[C:4]1[C:6]2=[CH:7][NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]2=[N:18][N:17]1[C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 8900HeptaneHCID 120894-Hydrazinobenzoic acidHCID 268963Ethyl 4-Chloroquinoline-3-carboxylate

Produkt 1

HCID 178524447HCID 178524447, VerbindungAusbeute 8,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 4-chloro-quinoline-3-carboxylic acid ethyl ester (11.8 mg, 0.5 mmol) and 4-hydrazino-benzoic acid (7.6 mg, 0.5 mmol) in n-butanol (0.5 mL) was stirred at 115° C. over night in a sealed tube. After cooling to 50-70° C., heptane (1.0 mL) was added and the product was allowed to crystallize upon further cooling to room temperature. The solvent was removed and the product was washed with heptane and dried under vacuum to yield 4-(3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoic acid (13 mg). 1H NMR (400 MHz, DMSO-d6) δ 12.9 (1H, s), 8.77 (1H, d), 8.38 (2H, d), 8.25 (1H, d), 8.03 (2H, d), 7.65-7.77 (2H, m), 7.58 (1H, t).

Aufarbeitung

  1. customto crystallize
  2. temperatureupon further cooling to room temperature
  3. customThe solvent was removed
  4. washthe product was washed with heptane
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-69af56a780f04c518b22da7aedf8bfda
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642249B2

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