Water → 5-Bromoquinoline-8-carboxylic acid

HRID 1189878

반응식

HRID 1189878 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 592928605-Bromoquinoline-8-carboxylic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-71aea8ddca434e29b51245e5503d1b0e
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674099B2

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