2,4-Dimethoxybenzylamine → 1-(2,4-Dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester 3-methyl ester

HRID 919767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919767
CO[C:3](=[O:20])[C:4]([C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][N:8]([CH3:10])C.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1CN>CCO>[CH3:19][O:18][C:16]([C:4]1[C:3](=[O:20])[N:8]([CH2:10][C:28]2[CH:27]=[CH:24][C:23]([O:22][CH3:21])=[CH:30][C:29]=2[O:31][CH3:32])[CH:7]=[CH:6][C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

Komponenten

4

Edukt 2

HCID 5972502,4-DimethoxybenzylamineHCID 851589875-Dimethylamino-3-ethoxycarbonyl-2-methoxycarbonyl-penta-2,4-dienoic acid methyl ester

Produkt 1

HCID 682975821-(2,4-Dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester 3-methyl esterAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5-dimethylamino-3-ethoxycarbonyl-2-methoxycarbonyl-penta-2,4-dienoic acid methyl ester (14.7 g, 51.7 mmol) and 2,4-dimethoxybenzylamine (8.2 mL, 54.3 mmol) in EtOH (90 mL) was refluxed for 5 h. The mixture was cooled to r.t., concentrated in vacuo, and the residual oil was partitioned between ether and 1 M HCl. The aqueous layer was extracted with additional ether, and the organic layers were combined, washed with water, and dried over MgSO4. Evaporation of the solvent in vacuo afforded 18.4 g of the title compound as a viscous orange oil. MS: (+) m/z 398.23 (M+Na).

Aufarbeitung

  1. temperaturewas refluxed for 5 h
  2. concentrationconcentrated in vacuo
  3. customthe residual oil was partitioned between ether and 1 M HCl
  4. extractionThe aqueous layer was extracted with additional ether
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-74338373cd4d4888b6f388f797699f48
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271970B2

Notizen zur Reaktion

Wird geladen…