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

HRID 1071793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071793
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-282c33d52117408a8de55c718bda050a
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906103B2

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