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

HRID 919768Notes

Reaction equation

HRID 919768 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-8abe92c17bd34dc0b9f2647224d2b2c3
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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