Hydrochloric Acid → 4-Chlorothieno[2,3-B]pyridine-5-carboxylic acid

HRID 1178612노트

반응식

HRID 1178612 반응식
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]2[S:13][CH:14]=[CH:15][C:3]=12.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]2[S:13][CH:14]=[CH:15][C:3]=12

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12376227Ethyl 4-chlorothieno[2,3-B]pyridine-5-carboxylate

생성물 1

HCID 113563314-Chlorothieno[2,3-B]pyridine-5-carboxylic acid수율 35.4%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

A mixture of ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate (800 mg, 3.31 mmol) [Khan, M. A.; Guarconi, A. E., J. Heterocyclic Chem., 14, 807 (1977)] in 15 mL of ethanol and 5 mL of 2.5 N sodium hydroxide is heated at reflux for 90 minutes. The mixture is cooled to 0° C. and the pH is adjusted to 4 by the addition of 2 N hydrochloric acid. The mixture is stirred at room temperature and the resulting precipitate is collected by filtration and washed with water to provide 250 mg of 4-chlorothieno[2,3-b]pyridine-5-carboxylic acid as a white solid, mp 172–174° C.; 1H NMR (DMSO-d6) δ 7.62 (d, J=6 Hz, 1H), 8.14 (d, J=6 Hz, 1H), 8.94 (s, 1H); MS 212.0 (M−H)−.

후처리

  1. temperatureat reflux for 90 minutes
  2. filtrationthe resulting precipitate is collected by filtration
  3. washwashed with water

출처 및 근거

ORD 기록
ord-ea5c08cf3d53462c83809f2f4de63499
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276519B2

반응 노트

불러오는 중…