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

HRID 919712Notes

Reaction equation

HRID 919712 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-a88e68b0f4a946fd9bfda50c1bc26fee
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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