Hydrochloric Acid → Toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester

HRID 502624ノート

反応式

HRID 502624 の反応式
[C:1]([C:4]1[C:13]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)(=[O:3])[CH3:2].[CH3:25][Mg]Cl.[NH4+].[Cl-].Cl>C1COCC1>[OH:3][C:1]([C:4]1[C:13]([O:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)([CH3:25])[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 86098625Toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl esterHCID 178418332HCID 178418332、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Toluene-4-sulfonic acid 2-acetyl-quinolin-3-yl ester (3.58 g, 10.5 mmol) in 40 mL of THF was cooled to around −20 to −25° C. Methyl magnesium chloride (5.25 mL of 3M solution in THF) was added dropwise over a period of 10 minutes. The reaction mixture was allowed to stir 18 hours at ambient temperature, and then was poured into saturated aqueous NH4Cl and acidified with 1N HCl to pH 5. The resulting mixture was extracted with ethyl acetate and the combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated to dryness under reduced pressure to give 3.75 g of toluene-4-sulfonic acid 2-(1-hydroxy-1-methyl-ethyl)-quinolin-3-yl ester as an oil that solidified on standing.

後処理

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-7b93517d03ef4298bef0557c4050d7aa
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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