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

HRID 47427

反応式

HRID 47427 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 539678632-Fluoroquinoline-4-carboxylic acid methyl ester収率 66.3%

試薬・触媒・溶媒 2

HCID 6213Dimethyl Sulfone溶媒HCID 21908982Water methylene chloride溶媒

反応条件

温度
180 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-c5db79bf0d3148d9bbb0dabc02bceb6e
出典データセット
uspto-grants-2004_03
特許番号
US06699879B1

関連ノート

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