Water → 1H-Indole, 6-methyl-

HRID 1798022

Reaktionsgleichung

Reaktionsgleichung von HRID 1798022
[C:1]([CH:3]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[N+:21]([O-])=O)C(OCC1C=CC=CC=1)=O)#N.O>[Pd].C(O)C>[CH3:20][C:17]1[CH:16]=[C:15]2[C:14]([CH:3]=[CH:1][NH:21]2)=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 962WaterHCID 10935797Benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate

Produkt 1

HCID 1379281H-Indole, 6-methyl-Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

a mixture of benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate (13 mmol), 5% palladium (0.84 g), water (4 mL) and ethanol (40 mL) is hydrogenated under 50 psi for 18 hours at 25° C. The catalyst is eliminated by filtration on celite and the solid is washed with ethanol. The filtrate obtained is evaporated under vacuum and the residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 2/1) in order to produce 6-methylindole with a yield of 74%.

Aufarbeitung

  1. filtrationThe catalyst is eliminated by filtration on celite
  2. washthe solid is washed with ethanol
  3. customThe filtrate obtained
  4. customis evaporated under vacuum
  5. customthe residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 2/1) in order

Quellen und Nachweise

ORD-Eintrag
ord-d89ffe2ad0ef44d999e2bc5fb2b3c936
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343964B2

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