Water → 4-Chloroquinoline-7-carboxylic acid

HRID 1432858노트

반응식

HRID 1432858 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](F)(F)F)=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH2:16].[OH-:17].[Na+]>OS(O)(=O)=O>[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1)([OH:17])=[O:16]

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 676684-Chloro-7-(trifluoromethyl)quinoline

생성물 1

HCID 217084474-Chloroquinoline-7-carboxylic acid

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

4-Chloro-7-trifluoromethylquinoline (5.0 g, 21.6 mmol) in 100 mL 80% H2SO4 is heated to 200° C. for 24 hours in a sealed tube. The solution is cooled, poured into water and neutralized with sodium hydroxide to pH˜3-4. The precipitated solid is collected, washed with water and dissolved in 2 N sodium hydroxide. The aqueous solution is washed with ethyl acetate then acidified to pH˜3-4. The precipitate is collected, washed with water and dried in a vacuum oven overnight to yield 7-carboxy-4-chloroquinoline as a solid (5.1 g, 24.6 mmol). A portion of this material (2.0 g, 9.6 mmol) is treated with anhydrous THF (200 mL) and DMF (2 mL) and 2 M oxalyl chloride in methylene chloride (14.5 mL, 29 mmol). The resulting suspension is stirred at room temperature for 2 h then treated with methanol (10 mL). After stirring 30 minutes the solution is concentrated and the residue is taken up in methylene chloride. The solution is washed with saturated sodium bicarbonate and dried (sodium sulfate) and concentrated to yield the title compound as a solid (2.1 g, 9.5 mmol). MS m/z: M+=221; 1H NMR (CDCl3, 300 MHz) δ8.6 (s, 1H), 8.2 (s, 1H), 7.9 (d, 1H), 7.65 (d, 1H), 7.45 (s, 1H), 3.95 (s. 3H).

후처리

  1. temperatureThe solution is cooled
  2. customThe precipitated solid is collected
  3. washwashed with water
  4. dissolutiondissolved in 2 N sodium hydroxide
  5. washThe aqueous solution is washed with ethyl acetate
  6. customThe precipitate is collected
  7. washwashed with water
  8. customdried in a vacuum oven overnight

출처 및 근거

ORD 기록
ord-ed15a0363f684b76a29efe3c730d9d87
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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