Ethanol → 2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 2196719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196719
[CH3:1][C:2]1[NH:13][C:5]2=[N:6][CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=[C:4]2[C:3]=1[CH3:14].[Cl-].[NH4+].C(O)C>[Fe].O>[CH3:1][C:2]1[NH:13][C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[C:3]=1[CH3:14]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 671560892,3-dimethyl-5-nitro-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 671560582,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2,3-Dimethyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.11 g, 0.596 mmol), iron (0.40 g, 7.16 mmol) and ammonium chloride (0.13 g, 2.39 mmol) were combined with ethanol (2.8 mL) and water (0.65 mL) in a microwave vessel and heated in a microwave reactor to 110° C. for 15 minutes. The reaction mixture was filtered, saturated aqueous sodium bicarbonate was added, and the layers were separated. The aqueous layer was extracted once with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo to afford 2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine (0.096 g, 100%), which was carried to the next step without further purification.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. additionsaturated aqueous sodium bicarbonate was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted once with ethyl acetate
  5. dry with materialThe organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-babc7a234d8f4e898c861bdcc819453c
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338452B2

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