Sodium Hydroxide → 4-Chloro-6-methylquinoline

HRID 394604

反応式

HRID 394604 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6][C:5]2=O.[OH-].[Na+].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[N:8]=[CH:7][CH:6]=1

参加物

4

反応物 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 2560804-Hydroxy-6-methylquinoline

生成物 1

HCID 8246244-Chloro-6-methylquinoline

実験手順

6-Methyl-(1H)-quinolin-4-one (1.57 g, 9.7 mmol) in 20 mL phosphorus oxychloride is heated to 110° C. for 4 hours. The mixture is cooled to room temperature then diluted with ice water (˜200 mL) and the pH is adjusted to ca. 10 by the slow addition of 10 N NaOH, The aqueous solution is extracted with methylene chloride (4×250 mL) and the combined organic layers washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue is filtered through silica gel with 33% EtOAc/hexanes to give the product (1.05 g, 5.9 mmol) as a yellow solid.

後処理

  1. extractionThe aqueous solution is extracted with methylene chloride (4×250 mL)
  2. washthe combined organic layers washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe crude residue is filtered through silica gel with 33% EtOAc/hexanes

出典と根拠

ORDレコード
ord-ef57d5d77a4c4837a34bd7d993f9c951
出典データセット
uspto-grants-2003_08
特許番号
US06602864B1

関連ノート

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