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Hydrochloric Acid → HCID 59129151, Verbindung

HRID 468436
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 468436
[CH3:1][C:2]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=2)([CH3:6])[C:3]([NH2:5])=O.Cl>C1COCC1>[CH3:6][C:2]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=2)([CH3:1])[CH2:3][NH2:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59129191HCID 59129191, Verbindung

Produkt 1

HCID 59129151HCID 59129151, VerbindungAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Methyl-2-(5-nitro-1H-indol-2-yl)propanamide (200 mg, 0.81 mmol) was suspended in THF (5 ml) and cooled to 0° C. Borane-THF complex solution (1.0 M, 2.4 mL, 2.4 mmol) was added slowly and the mixture was allowed to stir overnight at room temperature. The mixture was cooled to 0° C. and carefully acidified with 3 N HCl. THF was evaporated off, water was added and the mixture was washed with ethylacetate. The aqueous layer was made alkaline with 50% NaOH and the mixture was extracted with ethylacetate. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 2-methyl-2-(5-nitro-1H-indol-2-yl)propan-1-amine (82 mg, 43%).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. customTHF was evaporated off
  3. additionwater was added
  4. washthe mixture was washed with ethylacetate
  5. extractionthe mixture was extracted with ethylacetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-63d2dd7cba5042d58135b2f6268e2424
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08623905B2

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