Ethanol → 4-Bromo-5-methoxy-1H-indole-2-carboxylic acid

HRID 1791803ノート

反応式

HRID 1791803 の反応式
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[NH:6]2.[OH-].[K+].[CH2:19](O)C>O>[Br:1][C:2]1[C:10]([O:11][CH3:19])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[NH:6]2

参加物

5

反応物 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22030665Ethyl 4-bromo-5-hydroxyindole-2-carboxylate

生成物 1

HCID 133565154-Bromo-5-methoxy-1H-indole-2-carboxylic acid収率 96%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

Ethyl 4-bromo-5-hydroxyindole-2-carboxylate (1.49 g, 5 mmol.), (Jnl. Org. Chem. 1984, 49, 4761), was dissolved in ethanol (10 ml) and water (3.5 ml). Potassium hydroxide (840 mg) was added and the mixture stirred at 50° C. under an atmosphere of nitrogen for 1 hour then cooled to ambient temperature. The solvent was evaporated and the residue redissolved in water (25 ml). 2M Aqueous hydrochloric acid was added until the reaction mixture was at pH4, giving a precipitate which was filtered off, washed with water and dried under vacuum to give 4-bromo-5-methoxyindole-2-carboxylic acid (1.30, 96%).

後処理

  1. temperaturethen cooled to ambient temperature
  2. customThe solvent was evaporated
  3. dissolutionthe residue redissolved in water (25 ml)
  4. addition2M Aqueous hydrochloric acid was added until the reaction mixture
  5. customgiving a precipitate which
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-b0cff2d5040b4c34a8d7dbfcf7338615
出典データセット
uspto-grants-2006_07
特許番号
US07074800B1

反応ノート

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