Methanol → 8-Hydroxy-2-methyl-4-(trifluoromethyl)quinoline

HRID 1420633노트

반응식

HRID 1420633 반응식
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2[C:14]([F:17])([F:16])[F:15].B(Br)(Br)Br.CO.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2[C:14]([F:17])([F:15])[F:16]

참가 물질

6

반응물 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 187822278-Methoxy-2-methyl-4-trifluoromethylquinoline

생성물 1

HCID 187822758-Hydroxy-2-methyl-4-(trifluoromethyl)quinoline수율 79.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of 11 g (45.6.10-3 mol) of 8-methoxy-2-methyl-4-trifluoromethylquinoline in 360 ml of dichloromethane is cooled to -60° C. and 228 ml of a 1 M solution of boron tribromide in dichloromethane are added dropwise. The reaction medium is subsequently stirred for 1 hour at room temperature, 250 ml of methanol are then added slowly and stirring is continued for 2 hours. 250 ml of dichloromethane are added and sodium bicarbonate solution is added to render the medium alkaline. The organic phase is separated off, washed with water, dried over sodium sulfate and concentrated under reduced pressure to give 8.25 g of the expected product in the form of brown crystals (yield=79.5%).

후처리

  1. stirringstirring
  2. waitis continued for 2 hours
  3. customThe organic phase is separated off
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5bf05cf090114f1cbcd0596553a324db
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06071917

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