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Citric Acid → 1-(biphenyl-4-ylmethyl)-1H-indole-7-carboxylic acid

HRID 1909883
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1909883
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([O:19]C)=[O:18])[CH:10]=[CH:9]2)=[CH:3][CH:2]=1.CO.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([OH:19])=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58306447methyl 1-(biphenyl-4-ylmethyl)-1H-indole-7-carboxylate

Produkt 1

HCID 583069041-(biphenyl-4-ylmethyl)-1H-indole-7-carboxylic acidAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To methyl 1-(biphenyl-4-ylmethyl)-1H-indole-7-carboxylate (2.5 g) were added methanol (20 mL), THF (20 mL), and a 1 M aqueous sodium hydroxide solution (10 mL), followed by stirring at 60° C. for 16 hours. To the reaction mixture was added a 10% aqueous citric acid solution (20 mL), followed by extraction with ethyl acetate, and the organic layer was washed with brine. After dehydration over anhydrous sodium sulfate, filtering and concentrating under reduced pressure, the obtained residue was added with diisopropylether, solidified, and collected by filtration. This solid was purified by silica gel column chromatography (chloroform/methanol=99/1-97/3) to obtain 1-(biphenyl-4-ylmethyl)-1H-indole-7-carboxylic acid (0.99 g).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe organic layer was washed with brine
  3. filtrationAfter dehydration over anhydrous sodium sulfate, filtering
  4. concentrationconcentrating under reduced pressure
  5. additionthe obtained residue was added with diisopropylether
  6. filtrationcollected by filtration
  7. customThis solid was purified by silica gel column chromatography (chloroform/methanol=99/1-97/3)

Quellen und Nachweise

ORD-Eintrag
ord-c8ac8899574346d4910799310c63a32d
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08598355B2

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