Sodium Hydroxide → 1H-indole-2,5-dicarboxylic Acid

HRID 1071793ノート

反応式

HRID 1071793 の反応式
CC[O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[O:5].[OH-].[Na+]>O.CO>[NH:7]1[C:8]2[C:13](=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([OH:5])=[O:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 180713652-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid

生成物 1

HCID 43083261H-indole-2,5-dicarboxylic Acid収率 59%

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
50 °C

実験手順

Solution of 1H-Indole-2,5-dicarboxylic acid 2-ethyl ester# (20.0 g, 85.75 mmole) and NaOH (100 mmole) in a mixture of water/MeOH (1/1) (200 ml) was stirred at 50° C. for 4 h and then overnight at ambient temperature. The reaction mixture was evaporated in vacuo to dryness and the residue was dissolved in water (200 ml) and acidified with 1M HCl up to pH=3. The precipitates were collected on the filter and washed with water (3×50 ml) and dried over phosphorus pentoxide in dessicator to give indole-2,5-dicarboxylic acid 1 (10.38 g, 59%) of compound 1 as white crystals. MS: 203.7 (M−2H); 204.7 (M−H). 1H-NMR (DMSO-d6): 8.32 (m, 1H, H-4, indole); 7.80 (m, 1H, H-6, indole); 7.45 (d, 1H, H-7, indole); 7.22 (s, 1H, H-3, indole).

後処理

  1. customovernight
  2. customat ambient temperature
  3. customThe reaction mixture was evaporated in vacuo to dryness
  4. dissolutionthe residue was dissolved in water (200 ml)
  5. customThe precipitates were collected on the
  6. filtrationfilter
  7. washwashed with water (3×50 ml)
  8. dry with materialdried over phosphorus pentoxide in dessicator

出典と根拠

ORDレコード
ord-282c33d52117408a8de55c718bda050a
出典データセット
uspto-grants-2005_06
特許番号
US06906103B2

反応ノート

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