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 919767Notes

Reaction equation

HRID 919767 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 682975821-(2,4-Dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester 3-methyl esterYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-74338373cd4d4888b6f388f797699f48
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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