Hydrogen Peroxide → 2,6-Dichloro-5-cyclopropylnicotinamide

HRID 1020809

Reaktionsgleichung

Reaktionsgleichung von HRID 1020809
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7]([CH:11]2[CH2:13][CH2:12]2)=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=[O:15].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7]([CH:11]2[CH2:12][CH2:13]2)=[CH:6][C:3]=1[C:4]([NH2:5])=[O:15]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 848199202,6-Dichloro-5-cyclopropylnicotinonitrile

Produkt 1

HCID 866617192,6-Dichloro-5-cyclopropylnicotinamideAusbeute 838,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirred mixture of compound 2,6-dichloro-5-cyclopropylnicotinonitrile (1.10 g, 5.16 mmol) and K2CO3 (351 mg, 2.58 mmol) in DMSO (10 mL) was added 30% H2O2 (1.90 mL, 15.5 mmol). The mixture was stirred for 2 hrs at rt. Then the mixture was poured into water and extracted with EtOAc. The separated organics was dried, concentrated and purified by column chromatography (Petroleum ether:EtOAc=10:1˜1:1) to give compound 2,6-dichloro-5-cyclopropylnicotinamide (5 g, 70%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 7.69 (s, 1H), 6.70 (s, 1H), 6.20 (s, 1H), 2.08 (m, 1H), 1.18 (m, 2H), 0.69 (m, 2H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe separated organics was dried
  3. concentrationconcentrated
  4. custompurified by column chromatography (Petroleum ether:EtOAc=10:1˜1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2fcdffca458641cea1d3b1e20a251516
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716478B2

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