Hydrochloric Acid → 7-(benzyloxy)-1H-indole-2-carboxylic acid

HRID 1762941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1762941
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])C.[OH-].[Na+].Cl>O1CCCC1.CO>[CH2:16]([O:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13242189Ethyl 7-(benzyloxy)-1h-indole-2-carboxylate

Produkt 1

HCID 132421927-(benzyloxy)-1H-indole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 7-benzyloxyindole-2-carboxylic acid ethyl ester in 600 ml of tetrahydrofuran and 200 ml of methanol is combined with 500 ml of 2N sodium hydroxide solution and stirred for 3 hours at room temperature. The reaction mixture is then acidified under ice cooling with 10% hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases are dried, treated with active carbon, and concentrated. The residue is recrystallized from toluene, thus producing 35 g of 7-benzyloxyindole-2-carboxylic acid, mp 166°-168° C.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. customThe combined organic phases are dried
  3. additiontreated with active carbon
  4. concentrationconcentrated
  5. customThe residue is recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-0683743783254d79b789438005c81107
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04835175

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