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

HRID 502625ノート

反応式

HRID 502625 の反応式
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]

参加物

5

反応物 2

HCID 516892Sodium Bicarbonate2 回HCID 86611056Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 284Formic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c07a2b81b6724bf7a03e9e9481bef52e
出典データセット
uspto-grants-2010_08
特許番号
US07776872B2

反応ノート

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