Water → 5-Bromoquinoline-8-carboxylic acid

HRID 1189878

反応式

HRID 1189878 の反応式
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Br:7][C:8]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.[OH2:19]>N1C=CC=CC=1>[Br:7][C:8]1[CH:17]=[CH:16][C:15]([C:18]([OH:2])=[O:19])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

参加物

5

反応物 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 47150225-Bromo-8-methylquinoline

生成物 1

HCID 592928605-Bromoquinoline-8-carboxylic acid

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
110 °C

実験手順

A solution of potassium permanganate (18.2 g, 115.5 mmol, 2 equiv) in H2O (200 mL) was added to a hot (110° C.) solution of 5-bromo-8-methyl-quinoline (Step 159.4) (12.8 g, 57.7 mmol) in pyridine (120 mL). The reaction mixture was stirred for 10 min at 110° C. and filtered while hot. The residue in the filter was washed with H2O and pyridine. The filtrate was concentrated to remove pyridine, diluted with Et2O and basified by addition of a 2 N aqueous solution of NaOH (20 mL). The aqueous layer was separated and made acidic (pH 3) by addition of a 2 N aqueous solution of HCl. The resulting precipitate was collected by vacuum filtration to provide 1.45 g of the title compound as a green solid: ESI-MS: 251.9/253.9 [M+H]+; tR=3.56 min (System 1).

後処理

  1. filtrationfiltered while hot
  2. washThe residue in the filter was washed with H2O and pyridine
  3. concentrationThe filtrate was concentrated
  4. customto remove pyridine
  5. additiondiluted with Et2O
  6. additionbasified by addition of a 2 N aqueous solution of NaOH (20 mL)
  7. customThe aqueous layer was separated
  8. additionby addition of a 2 N aqueous solution of HCl
  9. filtrationThe resulting precipitate was collected by vacuum filtration

出典と根拠

ORDレコード
ord-71aea8ddca434e29b51245e5503d1b0e
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

関連ノート

読み込み中…