Lithium iodide → HCID 71282062, compound

HRID 1481684Notes

Reaction equation

HRID 1481684 reaction equation
[CH2:1]([C:3]1[C:4]([OH:25])=[C:5]([C:21]([O:23]C)=[O:22])[C:6](=[O:20])[NH:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH2:14][CH2:13][CH2:12]2)[CH3:2].[I-].[Li+]>CCOC(C)=O>[CH2:1]([C:3]1[C:4]([OH:25])=[C:5]([C:21]([OH:23])=[O:22])[C:6](=[O:20])[NH:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH2:14][CH2:13][CH2:12]2)[CH3:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 71284563HCID 71284563, compound

Product 1

HCID 71282062HCID 71282062, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
65 °C

Procedure

To a suspension of methyl 5-ethyl-4-hydroxy-6-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (34 mg, 0.1 mmol) in EtOAc (1 mL) was added lithium iodide (40 mg, ca. 0.3 mmol, 3.0 eq) at room temperature. The mixture was heated to 65° C. and stirred for 1 h. The reaction mixture was diluted by EtOAc (2 mL) then quenched with 1N HCl (0.5 mL). The precipitate was collected by filtration then washed with Et2O to afford the title compound as a yellow solid (20 mg, 0.061 mmol, 61%).

Workup

  1. customthen quenched with 1N HCl (0.5 mL)
  2. filtrationThe precipitate was collected by filtration
  3. washthen washed with Et2O

Sources & evidence

ORD record
ord-d65a66f24a76462198d42ae14b4f433d
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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