Sodium Hydroxide → 3-bromo-1H-indole-2-carboxylic acid

HRID 2292700ノート

反応式

HRID 2292700 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[Na+]>CCO.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([OH:13])=[O:12]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 4715017Ethyl 3-Bromoindole-2-carboxylate

生成物 1

HCID 23256883-bromo-1H-indole-2-carboxylic acid収率 96.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of ethyl 3-bromoindole-2-carboxylate (54.40 g, 203 mmol) in EtOH (600 ml) and water (50 ml) with NaOH (20.20 g, 505 mmol) was refluxed for 1 h. The mixture was cooled and the sodium salt of the title compound was removed by filtration. This was acidified (aqueous 3N HCl) and extracted with ethyl acetate. The organic extract was washed with water then brine, dried (sodium sulfate) and concentrated. Crystallization from ethyl acetate afforded the product (47.1 g, 88%). mp 201°-203° C.

後処理

  1. temperatureThe mixture was cooled
  2. customthe sodium salt of the title compound was removed by filtration
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialbrine, dried (sodium sulfate)
  7. concentrationconcentrated
  8. customCrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-3dbfb79717d441fd8d38915e8fbb7d05
出典データセット
uspto-grants-1997_11
特許番号
US05684032

反応ノート

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