Ethanol → 7-Methoxy-1H-indole-3-carboxylic acid

HRID 2165958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165958
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[CH2:13]([OH:15])C>[OH-].[Na+]>[CH3:13][O:15][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[C:3]2[C:10]([OH:12])=[O:11]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 69867Indole-3-Carboxylic Acid

Produkt 1

HCID 150679677-Methoxy-1H-indole-3-carboxylic acidAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Preparation of 5 was based on a procedure for the synthesis of indole-3-carboxylic acid reported by R. K. Mackie et al. [supra]. To a 200-mL round bottom flask, 2.369 g of 4 (9.75 mmol) was added. Compound 4 was dissolved in 19 mL of absolute ethanol and 53 mL of 5N aqueous sodium hydroxide, refluxed overnight, and allowed to cool. The ethanol was removed by rotary evaporation, and the resulting solution was extracted with two 25-mL portions of diethyl ether. The aqueous solution was acidified with concentrated hydrochloric acid, and the peach-colored precipitate was collected. Recrystallization from hot aqueous ethanol (50:50 ethanol:water) yielded 0.883 g (47%) of 5 as cream-colored crystals: 1H NMR (acetone-d6) δ 3.95 (s, 3H, OCH3), 6.76 (d, 1H, J=7.3 Hz), 7.10 (app. t, 1H, J=8 Hz), 7.71 (d, 1H, J=8.5 Hz), 7.95 (m, 1H), 11.0 (br s, 1H).

Aufarbeitung

  1. customPreparation of 5
  2. temperatureto cool
  3. customThe ethanol was removed by rotary evaporation
  4. extractionthe resulting solution was extracted with two 25-mL portions of diethyl ether
  5. customthe peach-colored precipitate was collected
  6. customRecrystallization from hot aqueous ethanol (50:50 ethanol:water)

Quellen und Nachweise

ORD-Eintrag
ord-a0bec0bbcecb4975a1ba53c583aa3c26
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04942247

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