Potassium Hydroxide → 6-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline

HRID 1505743

反応式

HRID 1505743 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Br:9])=[CH:4][C:3]=1[CH2:10]O.[CH3:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:21])=O)[CH:16]=[C:15]([CH3:22])[CH:14]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[Br:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[Cl:8])[N:1]=[C:19]([C:17]1[CH:18]=[C:13]([CH3:12])[CH:14]=[C:15]([CH3:22])[CH:16]=1)[CH:21]=[CH:10]2

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 67081018(2-Amino-5-bromo-4-chlorophenyl)methanol

生成物 1

HCID 866849816-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline収率 43.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

(2-amino-5-bromo-4-chlorophenyl)methanol (8.2 g, 34.7 mmol), 3,5-dimethylacetophenone (8.22 g, 55.5 mmol), RuCl2(PPh3)3 (0.15 g, 0.173 mmol), and KOH (1.31 g, 23.4 mmol) was refluxed in 90 mL of toluene for 18 hours. Water was collected from the reaction using a Dean-Stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with DCM and purified by column chromatography, eluting with 2:1 (v/v) hexanes:DCM, to give 6-bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline (5.2 g, 43.3%).

後処理

  1. customWater was collected from the reaction
  2. filtrationfiltered through a silica gel plug
  3. washeluted with DCM
  4. custompurified by column chromatography
  5. washeluting with 2:1 (v/v) hexanes

出典と根拠

ORDレコード
ord-5b3c372cda554e3b92366ec5f333ff36
出典データセット
uspto-grants-2015_12
特許番号
US09217004B2

関連ノート

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