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Hydrochloric Acid → 7-nitro-1H-indole-2-carboxylic acid

HRID 1515253
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1515253
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[N+:14]([O-:16])=[O:15])=[O:4].[OH-].[Na+].Cl>O1CCCC1.O>[N+:14]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13]2)([O-:16])=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18550960Methyl 7-nitro-1h-indole-2-carboxylate

Produkt 1

HCID 814097-nitro-1H-indole-2-carboxylic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

7-Nitro-1H-indole-2-carboxylic acid methyl ester (13 g, 59 mmol) prepared in Preparation 17 was dissolved in a solvent mixture of tetrahydrofuran and water (1:1, 300 mL), to which was added 1N aqueous sodium hydroxide solution (180 mL, 177 mmol). The mixture was stirred for 3 h at room temperature, and excess 6N hydrochloric acid solution was added thereto. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under reduced pressure, and the residue was dried to give the title compound (12 g, Yield 99%).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe residue was dried

Quellen und Nachweise

ORD-Eintrag
ord-fd3b8e134c0545f785950297efad3dfb
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222414B2

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