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

HRID 1259868ノート

反応式

HRID 1259868 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aed87ff42e3543caafecfc90ba252cdf
出典データセット
uspto-grants-2013_06
特許番号
US08466290B2

反応ノート

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