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

HRID 1410715Notes

Reaction equation

HRID 1410715 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:23])[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4].[Li+].[I-]>N1C=CC=CC=1>[CH2:14]([O:13][C:11]([C:10]1[CH:9]=[CH:8][N:7]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:6](=[O:23])[C:5]=1[C:3]([OH:4])=[O:2])=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 682974044-Ethyl 3-methyl 1-benzyl-1,2-dihydro-2-oxopyridine-3,4-dicarboxylate

Product 1

HCID 682975154-(Ethoxycarbonyl)-1-benzyl-1,2-dihydro-2-oxopyridine-3-carboxylic acidYield 59.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 1-benzyl-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester 3-methyl ester (5.77 g, 18.3 mmol) in 10 mL of pyridine was added to a refluxing mixture of LiI (9.8 g, 73.3 mmol) and 70 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 and acidified 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 3.3 g of the title compound as a yellow solid. 1H NMR (CDCl3, 200 MHz): δ=14.26 (s, 1H), 7.65 (d, 1H, J=7.0 Hz), 7.22-7.50 (m, 5H), 6.41 (d, 1H, J=6.8 Hz), 5.26 (s, 2H), 4.44 (q, 2H, J=7.6 Hz), 1.38 (t, 3H, J=7.0 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-5900e427b4414698a31fb2d050d6451f
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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