Benzylamine → 4-Benzylimino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester

HRID 279363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279363
C(OC([N:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14](=O)[CH2:13][CH:12]1[CH3:26])=O)C1C=CC=CC=1.C([N:29]([CH2:32][CH3:33])CC)C.[CH2:34](N)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:42](=[O:45])([O-])[O-:43].[K+].[K+]>[Ti](Cl)(Cl)(Cl)Cl.O.ClCCl>[CH2:34]([O:43][C:42]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14](=[N:29][CH2:32][C:33]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:26]=2)[CH2:13][CH:12]1[CH3:26])=[O:45])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

8

Edukt 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 15480673Benzyl 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Produkt 1

HCID 154806744-Benzylimino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl esterAusbeute 219,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

6,7-Dimethoxy-2-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (0.83 g, 2.3 mmol) was dissolved in a solution of triethylamine (2.2 mL, 2.3 mmol), benzylamine (0.55 mL, 5.1 mmol), and anhydrous dichloromethane (15 mL). This solution was stirred in a room temperature water bath as 2.5 mL of 1M solution of titanium tetrachloride (TiCl4) in dichloromethane (2.5 mmol) was slowly added. The reaction was allowed to stir at room temperature for 48 h. The reaction mixture was then poured into a stirred solution of water (50 mL) and potassium carbonate (10 g). After filtration, the filtrate was extracted with ethyl acetate (3×100 mL), the combined organic phases washed with water (100 mL), brine (50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give the desired imine (1.12 g, ca.100%). 1H NMR (CDCl3) δ1.2 (d, 3H), 2.7-2.9 (m, 2H), 3.7 (s, 3H), 3.9 (s, 3H), 4.6 (d, 1H), 4.7 (d, 1H), 5.0-5.2 (m, 2H), 5.4 (d, 1H), 7.2-7.5 (m, 11H), 7.8 (s, 1H).

Aufarbeitung

  1. additionwas slowly added
  2. filtrationAfter filtration
  3. extractionthe filtrate was extracted with ethyl acetate (3×100 mL)
  4. washthe combined organic phases washed with water (100 mL), brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8379157beda74ddfa0881a530b901186
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362198B1

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