Lithium hydroxide, monohydrate → 5-Chloro-2-(quinolin-6-yl)benzoic acid

HRID 2042103ノート

反応式

HRID 2042103 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)=[C:6]([CH:12]=1)[C:7]([O:9]CC)=[O:8].O[Li].O>C1COCC1.CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)=[C:6]([CH:12]=1)[C:7]([OH:9])=[O:8]

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 67253873Ethyl 5-chloro-2-(quinolin-6-yl)benzoate

生成物 1

HCID 672545235-Chloro-2-(quinolin-6-yl)benzoic acid収率 91%

試薬・触媒・溶媒 1

HCID 18504229Ethanol tetrahydrofuran water溶媒

実験手順

To a stirring solution of ethyl 5-chloro-2-(quinolin-6-yl)benzoate (0.244 g, 0.78 mmol) in 1:1:1 THF/EtOH/H2O (21 ml) at RT was added LiOH—H2O (0.164 g, 3.91 mmol). The resulting reaction mixture was stirred at RT overnight. Solvent was removed under reduced pressure and the residue was diluted with H2O (10 mL). The aqueous solution was acidified to pH˜4 with 3M HCl and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4) and concentrated to afford 5-chloro-2-(quinolin-6-yl)benzoic acid (0.201 g, 91% yield) as a white solid. MS (ESI) m/z: 284.0 (M+H+).

後処理

  1. customThe resulting reaction mixture
  2. customSolvent was removed under reduced pressure
  3. additionthe residue was diluted with H2O (10 mL)
  4. extractionextracted with EtOAc (3×30 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c627adf8e7b5469cb03f8c3c8cc837fc
出典データセット
uspto-grants-2013_11
特許番号
US08586565B2

反応ノート

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