Water → HCID 23019684, compound

HRID 1354189Notes

Reaction equation

HRID 1354189 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]3[C:16]([C:17]=2[CH3:18])=[C:15]([CH:19]2[CH2:21][CH2:20]2)[CH:14]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=[O:27])=[CH:4][CH:3]=1.CI.[C:30](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH:19]1([C:15]2[CH:14]=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12](=[O:27])[N:11]3[C:16]=2[C:17]([CH3:18])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH3:30])=[CH:7][CH:6]=2)[CH:9]=[CH:10]3)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23019679HCID 23019679, compound

Product 1

HCID 23019684HCID 23019684, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

50 mg of ethyl 8-(4-aminophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 2) was dissolved in 2 ml of DMF. 20 mg of methyl iodide and 29 mg of potassium carbonate were added to the obtained solution, and they were stirred at 70° C. for 17 hours. Water was added to the reaction mixture. After the extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by the silica gel column chromatography (eluent: chloroform/ethyl acetate=9/1) to obtain 16 mg of ethyl 1-cyclopropyl-9-methyl-8-(4-methylaminophenyl)-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. extractionAfter the extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by the silica gel column chromatography (eluent: chloroform/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-5da6a766c89a43fb8e434373f7abd5e0
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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