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Dichloromethane → 2-(4-Nitrophenyl)-4-quinolinecarboxylic acid methyl ester

HRID 1259861
ノート
印刷プレビュー

反応式

HRID 1259861 の反応式
C(Cl)Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N+:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([O-:14])=[O:13].[CH3:24][O:25][C:26]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30](Cl)[CH:29]=1)=[O:27]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C.O1CCOCC1>[CH3:24][O:25][C:26]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[C:30]([C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)[CH:29]=1)=[O:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27735524-Nitrophenylboronic acidHCID 5202936Methyl 2-chloroquinoline-4-carboxylate

生成物 1

HCID 34203702-(4-Nitrophenyl)-4-quinolinecarboxylic acid methyl ester収率 78.8%

試薬・触媒・溶媒 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 6228Dimethylformamide溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

PdCl2(dppf).CH2Cl2 (184 mg, 0.23 mmol), tripotassium phosphate (624 mg, 4.51 mmol), and 4-nitrophenylboronic acid (958 mg, 4.51 mmol) were added to a 1,4-dioxane (5 mL)/DMF (1 mL) mixed solution of 2-chloro-4-quinolinecarboxylic acid methyl ester (500 mg, 2.26 mmol) obtained in Reference Example 3, and the mixture was heated with stirring overnight at 85° C. in an argon atmosphere. After the reaction solution was concentrated, to the residue, a saturated aqueous solution of sodium chloride and methylene chloride were added, and insoluble matter was filtered off through celite. After that, the residue was subjected to extraction with methylene chloride and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography to obtain 2-(4-nitrophenyl)-4-quinolinecarboxylic acid methyl ester (549 mg, 1.78 mmol).

後処理

  1. customobtained in Reference Example 3
  2. temperaturethe mixture was heated
  3. concentrationAfter the reaction solution was concentrated, to the residue
  4. additiona saturated aqueous solution of sodium chloride and methylene chloride were added
  5. filtrationinsoluble matter was filtered off through celite
  6. extractionAfter that, the residue was subjected to extraction with methylene chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-eee545d12a32431c9e711717562ac72d
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466290B2

反応ノート

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