Potassium Fluoride → 2-Fluoroquinoline-4-carboxylic acid methyl ester

HRID 47427

반응식

HRID 47427 반응식
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7](Cl)[CH:6]=1)=[O:4].[F-:16].[K+]>CS(C)(=O)=O.ClCCl.O>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([F:16])[CH:6]=1)=[O:4]

참가 물질

5

반응물 2

HCID 522689Potassium FluorideHCID 5202936Methyl 2-chloroquinoline-4-carboxylate

생성물 1

HCID 539678632-Fluoroquinoline-4-carboxylic acid methyl ester수율 66.3%

시약·촉매·용매 2

HCID 6213Dimethyl Sulfone용매HCID 21908982Water methylene chloride용매

반응 조건

온도
180 °C

실험 절차

2-Chloroquinoline-4-carboxylic acid methyl ester (1.14 g) in dimethylsulfone (4.0 g) was treated with potassium fluoride (2.5 g) and heated at 180° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane:water (1:1, 200 ml), the organic phase separated, solvent removed at reduced pressure and the residue column chromatographed (silica gel, dichloromethane eluant) to give 2-fluoroquinoline-4-carboxylic acid methyl ester (0.7 g). 1H NMR (CDCl3) δ: 3.99 (3H, s), 7.57 (2H, m), 7.72 (1H, m), 7.95 (1H, d, J=8.5 Hz), 8.67 (1H, d, J=8.4 Hz). m/z (API+): 205 (MH+).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic phase separated
  3. customsolvent removed at reduced pressure
  4. customthe residue column chromatographed (silica gel, dichloromethane eluant)

출처 및 근거

ORD 기록
ord-c5db79bf0d3148d9bbb0dabc02bceb6e
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699879B1

연결된 노트

불러오는 중…