Hydrochloric Acid → 4,6-Dichloro-1H-indole-2-carboxylic acid

HRID 62647

反応式

HRID 62647 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[NH:6]2.C1COCC1.O[Li].O.Cl>O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[NH:6]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2 回HCID 168937Lithium hydroxide, monohydrateHCID 2736407ethyl 4,6-dichloro-1H-indole-2-carboxylate

生成物 1

HCID 1279884,6-Dichloro-1H-indole-2-carboxylic acid収率 87.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a solution of ethyl 4,6-dichloro-1H-indole-2-carboxylate (I-1c: 50 g, 193.72 mmol) in a solvent mixture consisting of THF & water (1:1) (900 mL) was added LiOH.H2O (24.41 g, 581.7 mmol) and the reaction mixture stirred at room temperature for 18h. The solvent (THF) was distilled-off, the residue was diluted with water (400 mL) and acidified with 2N aqueous HCl to pH 6.0. The residue was extracted in to ethyl acetate (4×150 mL), combined organic layer washed with brine (350 ml), dried on anhydrous Na2SO4 and concentrated under reduced pressure to obtain 39 g (87.5%) of 4,6-dichloro-1H-indole-2-carboxylic acid (I-1d) as light brown solid.

後処理

  1. extractionThe residue was extracted in to ethyl acetate (4×150 mL)
  2. washwashed with brine (350 ml)
  3. dry with materialdried on anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f784163e66c74023a560040e516453d4
出典データセット
uspto-grants-2016_09
特許番号
US09447039B2

関連ノート

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