Triethylamine → 1-Acetyl-4-[(benzoxazol-5-yl)imino]-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 1629674

Reaktionsgleichung

Reaktionsgleichung von HRID 1629674
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2].[NH2:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH:23]=[N:22][C:21]=2[CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[N:16][C:17]2[CH:18]=[CH:19][C:20]3[O:24][CH:23]=[N:22][C:21]=3[CH:25]=2)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 5895634(1H)-Quinolinone, 1-acetyl-2,3-dihydro-2-methyl-HCID 14821881,3-Benzoxazol-5-amine

Produkt 1

HCID 666251671-Acetyl-4-[(benzoxazol-5-yl)imino]-2-methyl-1,2,3,4-tetrahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

[Step 1] 177 mg of 1-acetyl-4-oxo-2-methyl-1,2,3,4-tetrahydroquinoline and 77 mg of 5-aminobenzoxazole were dissolved in 2 mL of methylene chloride, and 0.32 mL of triethylamine and 0.57 mL of titanium tetrachloride (1.0 M dichloromethane solution) were added to the solution under ice cooling. The mixture was stirred for 16 hours at room temperature. After completion of the reaction, the reaction liquid was filtered through Celite, and was concentrated under reduced pressure. Thus, a crude product of 1-acetyl-4-[(benzoxazol-5-yl)imino]-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a pale brown solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. filtrationwas filtered through Celite
  4. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fd753f7fcee6499ea2392a280f58a010
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791090B2

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