Sodium Chloride → 6-Cyano-2-phenyl-4-quinolinecarboxylic acid methyl ester

HRID 1259868Notes

Reaction equation

HRID 1259868 reaction equation
[CH3:1][N:2](C)C=O.[CH3:6][O:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](Br)[CH:18]=2)[N:13]=[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]=1)=[O:9].[Cl-].[Na+]>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:6][O:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:1]#[N:2])[CH:18]=2)[N:13]=[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]=1)=[O:9]

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 4066917Methyl 6-bromo-2-phenylquinoline-4-carboxylate

Product 1

HCID 672044376-Cyano-2-phenyl-4-quinolinecarboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Zinc cyanide (0.3394 g, 2.89 mmol) and tetrakis(triphenylphosphine)palladium (0.1647 g, 0.143 mmol) were added to a dimethylformamide (14.0 mL) solution of 6-bromo-2-phenyl-4-quinolinecarboxylic acid methyl ester (0.9749 g, 2.85 mmol), and the mixture was heated with stirring at 150° C. for 10 minutes with microwave irradiation. To the reaction solution, water and a saturated aqueous solution of sodium chloride were added. The mixture was subjected to extraction with ethyl acetate and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography, and the solvent was distilled off to obtain 6-cyano-2-phenyl-4-quinolinecarboxylic acid methyl ester (0.6614 g, 2.29 mmol) as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. extractionThe mixture was subjected to extraction with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe obtained residue was purified by silica gel column chromatography
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-aed87ff42e3543caafecfc90ba252cdf
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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