Ethanol → HCID 57917364、化合物

HRID 1942057ノート

反応式

HRID 1942057 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.O[CH2:13][CH:14]([CH2:16]O)O.[CH3:18][CH2:19][OH:20].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH2:18]([O:7][C:6]([C:5]1[C:4]([F:11])=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:16][CH:14]=[CH:13]2)=[O:8])[CH3:19].[CH2:19]([O:20][C:6]([C:5]1[CH:9]=[C:10]2[C:2](=[CH:3][C:4]=1[F:11])[N:1]=[CH:16][CH:14]=[CH:13]2)=[O:8])[CH3:18]

参加物

7

反応物 4

HCID 702EthanolHCID 753GlycerolHCID 14923Ammonium HydroxideHCID 3026804-Amino-2-fluorobenzoic acid

生成物 2

HCID 57917364HCID 57917364、化合物HCID 57917442Ethyl 5-fluoro-6-quinolinecarboxylate

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
100 °C

実験手順

To a suspension of 4-amino-2-fluoro-benzoic acid (1 g, 6.38 mmol) in sulfuric acid 75% (15 mL) were added glycerol anhydrous (2.108 mL, 28.72 mmol) and sodium 3-nitrosulfonate (2.93 g, 12.8 mmol). The mixture was stirred at 100° C. for 4 h. It was then cooled down to 60° C. and EtOH was added. The mixture was then stirred at 60° C. for 45 h. The solution was poured into ice-water mixture and then basified with saturated aqueous ammonium hydroxide. It was extracted twice with EtOAc. The organic phases were joined and washed with brine, dried over Na2SO4 and concentrated. The residue was purified by MPLC eluting with a DCM/MeOH gradient to afford a yellow oil as a mixture (1:1) of 5-fluoro-quinoline-6-carboxylic acid ethyl ester and 7-fluoro-quinoline-6-carboxylic acid ethyl ester (tR 1.3 min and tR 1.1 min (conditions 6), MH+=220).

後処理

  1. temperatureIt was then cooled down to 60° C.
  2. stirringThe mixture was then stirred at 60° C. for 45 h
  3. extractionIt was extracted twice with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC
  8. washeluting with a DCM/MeOH gradient

出典と根拠

ORDレコード
ord-f0b0b54082d04dc49ccfbc5bd890a6cb
出典データセット
uspto-grants-2013_03
特許番号
US08389526B2

反応ノート

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