Cesium carbonate → 2-(1,3-Benzodioxol-5-yloxy)pyridine-3-carboxylic acid

HRID 350972

반응식

HRID 350972 반응식
C([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1Cl)C.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=2[O:15][CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[OH-].[Li+].O>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([O:22][C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4]([OH:3])=[O:12])=[CH:21][C:16]=2[O:15][CH2:14]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 68289SesamolHCID 2796614Ethyl chloronicotinate

생성물 1

HCID 27368792-(1,3-Benzodioxol-5-yloxy)pyridine-3-carboxylic acid

시약·촉매·용매 3

HCID 962Water용매HCID 3939Lithium Hydroxide용매HCID 312751,4-Dioxane용매

실험 절차

2-Chloro-nicotinic acid ethyl ester (10 g), benzo[1,3]dioxol-5-ol (sesamol, 8.2 g), and cesium carbonate (21 g) were mixed in anhydrous dioxane (40 mL) and the resulting slurry heated to reflux for 16 h. In a separate flask, lithium hydroxide (12.9 g) was dissolved in water (80 mL) with warming and then added to the refluxing mixture, which was heated for an additional 4 h. The mixture was cooled to ambient temperature and concentrated in vacuo to remove the dioxane. Concentrated hydrochloric acid was added dropwise until the pH=3. The acidified solution was then extracted with ethyl acetate (7×100 mL) to yield crude product, which was recrystallized from ethyl acetate to yield the purified title compound (10.8 g).

후처리

  1. temperaturethe resulting slurry heated
  2. temperatureto reflux for 16 h
  3. temperaturewith warming
  4. additionadded to the refluxing mixture, which
  5. temperaturewas heated for an additional 4 h
  6. concentrationconcentrated in vacuo
  7. customto remove the dioxane
  8. additionConcentrated hydrochloric acid was added dropwise until the pH=3
  9. extractionThe acidified solution was then extracted with ethyl acetate (7×100 mL)
  10. customto yield crude product, which
  11. customwas recrystallized from ethyl acetate
  12. customto yield the
  13. custompurified title compound (10.8 g)

출처 및 근거

ORD 기록
ord-d393aad1e2d34ab7a46739b8c9a67895
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183293B2

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