Sulfuric Acid → HCID 19026184, 화합물

HRID 1195167노트

반응식

HRID 1195167 반응식
S(=O)(=O)(O)O.O[C:7]1([CH3:25])[CH2:16][CH2:15][CH2:14][C:13]2[N:12]=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=[CH:9][C:8]1=2.[OH-:26].[Na+].[C:28](#[N:30])[CH3:29]>>[CH3:25][C:7]1([NH:30][C:28](=[O:26])[CH3:29])[CH2:16][CH2:15][CH2:14][C:13]2[N:12]=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=[CH:9][C:8]1=2

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 10061627HCID 10061627, 화합물

생성물 1

HCID 19026184HCID 19026184, 화합물수율 16%

실험 절차

Conc sulfuric acid (70 ml) was added dropwise over 45 mins to a solution of 5,6,7,8-tetrahydro-5-hydroxy-5-methyl-2-(phenylmethoxy)quinoline (14.0 g) and acetonitrile (200 ml) at 0° C. The solution was stirred at room temperature for 18 hrs, poured over ice, and basified to pH 8 with 50% sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was purified by colmn chromatography (silica gel, elution with ethyl acetate). The appropriate fractions were collected and evaporated. Recrystallization (twice) of the residue from ethyl acetate/hexanes gave 2.60 g (16%) of product, mp 153°-154° C.

후처리

  1. additionpoured over ice
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by colmn chromatography (silica gel, elution with ethyl acetate)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customRecrystallization (twice) of the residue from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-1af7e26c28df484da406ebb042c50891
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110815

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