Dichloromethane → cis-4-(Acetyl-phenylamino)-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester

HRID 1352488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352488
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][C@@H:12]1[CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH:35]([CH3:37])C)CC)(C)C.ClCCl.C(=O)([O-])[O-:42].[K+].[K+]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([N:21]([C:35](=[O:42])[CH3:37])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][C@@H:12]1[CH3:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 12093188cis-2-Methyl-4-phenylamino-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester

Produkt 1

HCID 12093189cis-4-(Acetyl-phenylamino)-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl esterAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of cis-2-methyl-4-phenylamino-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (5.3 g), diisopropyl ethyl amine (2.73 g) in dioxane (31 ml), anhydride acetic (7.26 g) was added under stirring. The mixture was heated under reflux over night. After cooling, dichloromethane and an aqueous solution of potassium carbonate were added. The organic layer was separated, and then dried over sodium sulfate. Organic solvent was removed under reduce pressure to give the crude compound (18 g). The desired compound (3.8 g, 64% yield) was obtained after purification by flash chromatography on silica gel with cyclohexane/ethyl acetate (80/20) as eluent and then cyclohexane/ethyl acetate (50/50).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux over night
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customOrganic solvent was removed
  7. customto give the crude compound (18 g)

Quellen und Nachweise

ORD-Eintrag
ord-4072c7e77be0403e82a36a5059fec4ae
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220760B2

Notizen zur Reaktion

Wird geladen…