Water → Ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 535472Notes

Reaction equation

HRID 535472 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH3:9][C:10]1[CH:11]=[C:12]2[N:17]([C:18]=1[C:19]([C:21]1[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:24]3=[O:36])=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13]2.O>CN(C=O)C>[CH3:9][C:10]1[CH:11]=[C:12]2[N:17]([C:18]=1[C:19]([C:21]1[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=1)[N:27]([CH3:1])[CH:26]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:24]3=[O:36])=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 66653314Ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 66652940Ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1.53 g (11.12 mmol) of potassium carbonate and 0.69 ml (11.12 mmol) of methyl iodide are added, at ambient temperature under an inter atmosphere, to 3.73 g (9.27 mmol) of ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate in 100 ml of DMF. The reaction medium is heated at 90° C. for 2 h. 0.384 g (2.78 mmol) of potassium carbonate and 0.173 ml (2.78 mmol) of methyl iodide are added and then the heating is continued for 40 minutes. The reaction medium is hydrolysed with water and then extracted with ethyl acetate and with dichloromethane. The organic phase is washed with a saturated solution of sodium chloride, dried over sodium sulphate, and then concentrated under reduced pressure. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (90/10) mixture. 3.15 g of a yellow solid are obtained.

Workup

  1. extractionextracted with ethyl acetate and with dichloromethane
  2. washThe organic phase is washed with a saturated solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-c1c23ad86939454a9a14ae50864b4a7f
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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