Lithium iodide → 1-(2,4-Dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester

HRID 1410771Notes

Reaction equation

HRID 1410771 reaction equation
C[O:2][C:3]([C:5]1[C:6](=[O:27])[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[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:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[C:6](=[O:27])[C:5]=1[C:3]([OH:4])=[O:2])=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 682975821-(2,4-Dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester 3-methyl ester

Product 1

HCID 682976311-(2,4-Dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl esterYield 74.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 1-(2,4-dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester 3-methyl ester (18.4 g, 49.0 mmol) in 30 mL of pyridine was added to a refluxing mixture of LiI (26.2 g, 196 mmol) in 190 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 dissolved in water (200 mL) and acidified with 6M HCl to pH about 2. The resulting precipitate was collected by filtration. The crude product was purified by chromatography (100% EtOAc) to give 13.2 g of the title compound. MS: (+) m/z 384.29 (M+Na).

Workup

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. customsolvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water (200 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. customThe crude product was purified by chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-e17f6c8a60cb4ef4881159e83c3aae48
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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