Triethylamine → diethyl 3-(m-chlorophenyl)-4-methyl-2-oxo-2H-pyrano[2,3-b]pyridine-6,7-dicarboxylate

HRID 1733836

Reaktionsgleichung

Reaktionsgleichung von HRID 1733836
[C:1]([C:4]1[C:9](=O)[NH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=1)(=O)[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH2:28][C:29]([OH:31])=[O:30])[CH:25]=[CH:26][CH:27]=1.C(N(CC)CC)C.[OH-].[NH4+]>C(OC(=O)C)(=O)C>[Cl:21][C:22]1[CH:23]=[C:24]([C:28]2[C:29](=[O:31])[O:30][C:9]3=[N:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[C:4]3[C:1]=2[CH3:2])[CH:25]=[CH:26][CH:27]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 158793-Chlorophenylacetic acidHCID 13752508Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Produkt 1

HCID 19958197diethyl 3-(m-chlorophenyl)-4-methyl-2-oxo-2H-pyrano[2,3-b]pyridine-6,7-dicarboxylateAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate (12.0 g, 0.043 mol), 3-chlorophenyl acetic acid (7.33 g, 0,043 mol) and triethylam ine (6.52 g) are refluxed in 120 mL of acetic anhydride for three hours. The reaction mixture is cooled, poured into 120 mL of ice-cold water and made alkaline to pH 8 with an ammonium hydroxide solution. The crystallin e solid is filtered and washed with water to give (17.0 g, 95%) of the product after drying. Recrystallization from ethyl acetate affords the pure product (13.29, 74% yield), melting point 170°-172° C.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe crystallin e solid is filtered
  3. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-c882dd96fdfa458baf18b154ac942719
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05532207

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