Diethyl Ether → HCID 54381814, Verbindung

HRID 580810

Reaktionsgleichung

Reaktionsgleichung von HRID 580810
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH2:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[F:14][C:15]([F:28])([F:27])[C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1[CH:18]=[CH:19][C:20](Cl)=[O:21].C(OCC)C>C(O)(=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:20](=[O:21])[CH:19]=[CH:18][C:17]3[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=3[C:15]([F:27])([F:28])[F:14])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 2239952-Methylquinoline-4,6-diamineHCID 533961253-[2-(Trifluoromethyl)phenyl]prop-2-enoyl chloride

Produkt 1

HCID 54381814HCID 54381814, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

4,6-Diamino-2-methyl-quinoline (0.5 g, 2.9 mmol) was placed in an oven-dried 100-mL three-necked flask under nitrogen followed by 3 mL of glacial acetic acid. A solution of 2-(trifluoro-methyl)cinnamoyl chloride (0.68 g, 2.89 mmol) in 1 mL of glacial acetic acid was added dropwise over a 2 min period to this mixture. A heavy precipitate resulted. The mixture was stirred at room temperature for 1 hr, diethyl ether (25 mL) added, and the hydrochloride salt filtered, washed with ether, and dried at room temperature in vacuo. The hydrochloride salt was dissolved in a warm mixture of 50% aqueous methanol and the solution filtered. The solution was made basic with sodium bicarbonate solution and the resulting solid filtered, washed with water, and dried at 50° C. under high vacuum. Recrystallization from hot methanol gave 0.68 g (63%) of the desired product; m.p. 272-273°.

Aufarbeitung

  1. customA heavy precipitate resulted
  2. filtrationthe hydrochloride salt filtered
  3. washwashed with ether
  4. customdried at room temperature in vacuo
  5. dissolutionThe hydrochloride salt was dissolved in a warm mixture of 50% aqueous methanol
  6. filtrationthe solution filtered
  7. filtrationthe resulting solid filtered
  8. washwashed with water
  9. customdried at 50° C. under high vacuum
  10. customRecrystallization from hot methanol

Quellen und Nachweise

ORD-Eintrag
ord-1a49bf1c3bd94198a1423b07d0172c5f
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919776

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