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

HRID 1505743

반응식

HRID 1505743 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5b3c372cda554e3b92366ec5f333ff36
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09217004B2

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