Lithium iodide → 3-(Ethoxycarbonyl)-1-benzyl-1,2-dihydro-2-oxopyridine-4-carboxylic acid

HRID 1410754Notes

Reaction equation

HRID 1410754 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:18])[C:6]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:4].[Li+].[I-]>N1C=CC=CC=1>[CH2:22]([O:21][C:19]([C:6]1[C:7](=[O:18])[N:8]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:2])=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 682972791-Benzyl-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 3-ethyl ester 4-methyl ester

Product 1

HCID 682973793-(Ethoxycarbonyl)-1-benzyl-1,2-dihydro-2-oxopyridine-4-carboxylic acidYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 1-benzyl-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 3-ethyl ester 4-methyl ester (4.1 g, 13 mmol) in 10 mL of pyridine was added to a refluxing mixture of LiI (7.0 g, 52 mmol) and 50 mL of pyridine. The resulting mixture was refluxed for 1 h. After the mixture was cooled to r.t., solvent was evaporated in vacuo. The residue was taken up in water (150 mL) and acidified to pH about 2 with 6M HCl. The resulting suspension was extracted several times with CHCl3, and the organic layers were combined and dried over MgSO4. After solvent was evaporated in vacuo, the crude product was chromatographed (100% EtOAc) to give 1.8 g of the title compound as a yellow solid. 1H NMR (CDCl3, 200 MHz): δ=7.20-7.45 (m, 6H), 6.61 (d, 1H, J=7.0 Hz), 5.16 (s, 2H), 4.41 (q, 2H, J=7.4 Hz), 1.37 (t, 3H, J=6.2 Hz).

Workup

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. customsolvent was evaporated in vacuo
  3. extractionThe resulting suspension was extracted several times with CHCl3
  4. dry with materialdried over MgSO4
  5. customAfter solvent was evaporated in vacuo
  6. customthe crude product was chromatographed (100% EtOAc)

Sources & evidence

ORD record
ord-ce5109e8c0e24b239160a8c3e0e0c534
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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