Sodium Bicarbonate → Toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester

HRID 502625노트

반응식

HRID 502625 반응식
O[C:2]([C:5]1[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)([CH3:4])[CH3:3].C([O-])(O)=O.[Na+]>C(O)=O.[Zn]>[CH:2]([C:5]1[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:17])=[O:18])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)([CH3:4])[CH3:3]

참가 물질

5

반응물 2

HCID 516892Sodium Bicarbonate2회HCID 86611056Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester

생성물 1

HCID 86611057Toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester수율 37.7%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 284Formic Acid용매

실험 절차

Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester (3.75 g, 10.5 mmol) was stirred in 50 mL of formic acid for 10 minutes, and zinc dust (3.43 g, 5.25 mmol) was added. The reaction mixture was stirred for four hours and then was added cautiously to a mixture of 100 mL aqueous saturated NaHCO3 and 100 g of ice. The resulting aqueous mixture was neutralized to pH7 by addition of aqueous saturated NaHCO3, and was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography using silica eluting with 10% ethyl acetate in hexanes to afford 1.35 g of toluene-4-sulfonic acid 2-isopropyl-quinolin-3-yl ester.

후처리

  1. extractionwas extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-c07a2b81b6724bf7a03e9e9481bef52e
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776872B2

반응 노트

불러오는 중…