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

HRID 1259868노트

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HRID 1259868 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

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온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aed87ff42e3543caafecfc90ba252cdf
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466290B2

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