Hydrogen Peroxide → 4-Propylpicolinonitrile

HRID 1268997

Reaktionsgleichung

Reaktionsgleichung von HRID 1268997
[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].OO.C[Si]([C:16]#[N:17])(C)C.CN(C)C(Cl)=O>C(=O)([O-])[O-].[K+].[K+]>[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:16]#[N:17])[CH:5]=1)[CH2:2][CH3:3]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 6598Dimethylcarbamoyl ChlorideHCID 707384-PropylpyridineHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 230032234-PropylpicolinonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

To 4-propylpyridine (TCI) (2.5 g, 20 mmol), 30% hydrogenperoxide (2.4 g) was added and refluxed overnight. The solvent was removed and the resulting residue was taken in DCM (30 mL). Trimethylsilyl cyanide (2.6 g, 26 mmol) was added to the above solution followed by dimethyl carbamyl chloride (2.8 g, 26 mmol) and left stirred at room temperature overnight. Potassium carbonate (10%, 100 mL) was added. The organic layer was separated, dried over sodium sulfate and then concentrated to obtain 4-propyl-2-cyanopyridine (2.5 g, 93%). It was then refluxed in hydrochloric acid (6N, 60 mL) for overnight. The 4-propylpyridinecarboxylic acid 10b (R9=nPr) was obtained after crystallization from acetonitrile (2.0 g, 71%): MS (ESPOS): 166 [M+H]; 1H NMR (300 MHz, CD3OD) δ 8.75 (dd, J=9.0, 3.0, 1), 8.42 (s, 1), 8.08 (dd, J=9.0, 3.0, 1), 3.00 (t, J=7.5, 2), 1.82 (m, 2), 1.05 (t, J=7.2, 3).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customThe solvent was removed
  3. waitleft
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fc22799335f548f8b26d1446c0ae665b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199106B2

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