Sulfuric Acid → HCID 19026184、化合物

HRID 1195167ノート

反応式

HRID 1195167 の反応式
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

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 10061627HCID 10061627、化合物

生成物 1

HCID 19026184HCID 19026184、化合物収率 16%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1af7e26c28df484da406ebb042c50891
出典データセット
uspto-grants-1992_05
特許番号
US05110815

反応ノート

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