Methyl iodide → HCID 86732725, compound

HRID 525859Notes

Reaction equation

HRID 525859 reaction equation
[C:1]([C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[C:1]([C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=2)[N:6]([CH3:20])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3245723HCID 3245723, compound

Product 1

HCID 86732725HCID 86732725, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of ethyl 3-acetyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (5.74 g, 22.14 mmol) in N,N-dimethylformamide (120 ml) was added potassium carbonate (9.18 g, 66.4 mmol) and methyl iodide (4.2 ml, 67.2 mmol). The mixture was stirred at 90° C. for 1 h. After cooling, the reaction was filtered, concentrated under high vacuum, diluted with dichloromethane/ethyl acetate, and filtered through a silica plug to afford ethyl 3-acetyl-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (3.64 g, 13.32 mmol, 60.2% yield. LCMS: (M+H)+: 274.0.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated under high vacuum
  4. additiondiluted with dichloromethane/ethyl acetate
  5. filtrationfiltered through a silica plug

Sources & evidence

ORD record
ord-30654b44d6e248f79301f3016b5d1fe6
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

Loading…