Benzylamine → 1-Benzyl-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 3-ethyl ester 4-methyl ester

HRID 919750Notes

Reaction equation

HRID 919750 reaction equation
C(O[C:4](=[O:21])[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][N:9]([CH3:11])C)C.C(N)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[CH3:15][O:14][C:12]([C:6]1[CH:7]=[CH:8][N:9]([CH2:11][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4](=[O:21])[C:5]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:13]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 867141145-Dimethylamino-2-ethoxycarbonyl-3-methoxycarbonyl-penta-2,4-dienoic acid ethyl ester

Product 1

HCID 682972791-Benzyl-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 3-ethyl ester 4-methyl esterYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-dimethylamino-2-ethoxycarbonyl-3-methoxycarbonyl-penta-2,4-dienoic acid ethyl ester (5 g, 16.7 mmol) and benzylamine (1.9 mL, 17.6 mmol) in MeOH (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 1 M HCl and water, and then dried over MgSO4. Evaporation of the solvent in vacuo afforded 4.1 g of the title compound as a dark brown oil. 1H NMR (CDCl3, 200 MHz): δ=7.20-7.40 (m, 6H), 6.56 (d, 1H, J=7.0 Hz), 5.15 (s, 2H), 4.42 (q, 2H, J=7.4 Hz), 3.88 (s, 3H), 1.40 (t, 3H, J=7.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-d1c645e9f22e4902ba17532a60975343
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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