Potassium Hydroxide → cis-4-amino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 279365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279365
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9](=[N:20]O)[CH2:8][CH:7]1[CH3:22])=[O:5])[CH3:2].[OH-].[K+]>C(O)C.[Al].[Ni]>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([NH2:20])[CH2:8][C@@H:7]1[CH3:22])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 867559824-Hydroxyimino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

Produkt 1

HCID 69832909cis-4-amino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6336846Nickel aluminideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-hydroxyimino-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (11.0 g, 34.1 mmol) in ethanol (100 mL) and aqueous 2N KOH (102 mL, 205 mmol) was added aluminum-nickel alloy (11.7 g, 136 mmol) in portions over 15 min. The reaction was stirred for 35 min, then filtered through a pad of Celite®, rinsing with ethanol. The volatiles were removed in vacuo, and the resulting aqueous phase was extracted with ethyl acetate (3×150 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 16.32 g of crude product. Purification by silica gel chromatography using 0-4% methanol in dichloromethane as eluent afforded the title compound (6.51 g, 65%): 1H NMR (CDCl3) δ1.19 (d, 3H, J=6 Hz), 1.25 (m, 1H), 1.28 (t, 3H, J=7 Hz), 2.4 (m, 1H), 3.76 (m, 1H), 3.86 (s, 3H), 3.90 (s, 3H), 4.10-4.35 (m, 2H), 4.5 (m, 1H), 6.96 (s, 1H), 7.0 (s, 1H).

Aufarbeitung

  1. filtrationfiltered through a pad of Celite®
  2. washrinsing with ethanol
  3. customThe volatiles were removed in vacuo
  4. extractionthe resulting aqueous phase was extracted with ethyl acetate (3×150 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give 16.32 g of crude product
  10. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6791be4bb82f4c18bb631d7733e4ae42
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362198B1

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