Benzylamine → 4-Ethyl 3-methyl 1-benzyl-1,2-dihydro-2-oxopyridine-3,4-dicarboxylate

HRID 919711Notes

Reaction equation

HRID 919711 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.C(N)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCO>[CH3:19][O:18][C:16]([C:4]1[C:3](=[O:20])[N:8]([CH2:10][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=[CH:6][C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 851589875-Dimethylamino-3-ethoxycarbonyl-2-methoxycarbonyl-penta-2,4-dienoic acid methyl ester

Product 1

HCID 682974044-Ethyl 3-methyl 1-benzyl-1,2-dihydro-2-oxopyridine-3,4-dicarboxylateYield 104.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-dimethylamino-3-ethoxycarbonyl-2-methoxycarbonyl-penta-2,4-dienoic acid methyl ester (5 g, 17.5 mmol) and benzylamine (2 mL, 18.4 mmol) in EtOH (30 mL) was refluxed for 5 h. The mixture was cooled to r.t., concentrated in vacuo, and taken up in ether. The solution was washed with 1M HCl and water, and then dried over MgSO4. Evaporation of the solvent in vacuo afforded 5.77 g of the title compound as a viscous orange oil. MS: (+) m/z 338.06 (M+Na).

Workup

  1. temperaturewas refluxed for 5 h
  2. concentrationconcentrated in vacuo
  3. washThe solution was washed with 1M HCl and water
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-e1b1b619a05842e891885dcc2d6971ef
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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