Hydrochloric Acid → 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylic acid

HRID 1054663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054663
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]C)=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1.CO.[OH-].[Na+].Cl>C(OCC)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 14798Sodium HydroxideHCID 86698666methyl 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylate

Produkt 1

HCID 866986676-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylic acidAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylate (75 mg, 0.22 mmol), methanol (2.2 mL), and aqueous sodium hydroxide (1 M, 0.75 mL, 0.75 mmol) was heated at 75° C. for 24 hours. The reaction was acidified with 1 M HCl to pH=2 then diluted with ethyl acetate. The aqueous layer was back-extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a crude solid. The crude product was dissolved in methylene chloride and methanol and silica gel was added. The solvent was removed in vacuo and the crude material adsorbed onto silica was loaded onto a column of silica gel and eluted with ethyl acetate (with 0.2% formic acid)/heptanes (1:1 to 1:0) to provide the title compound (17 mg, 24%) as a tan solid.

Aufarbeitung

  1. extractionThe aqueous layer was back-extracted twice with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a crude solid
  6. customThe solvent was removed in vacuo
  7. washeluted with ethyl acetate (with 0.2% formic acid)/heptanes (1:1 to 1:0)

Quellen und Nachweise

ORD-Eintrag
ord-ecc5855cb67847c38ba53629fdd16862
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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