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

HRID 1071793노트

반응식

HRID 1071793 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 43083261H-indole-2,5-dicarboxylic Acid수율 59%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-282c33d52117408a8de55c718bda050a
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906103B2

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