Hydrogen Peroxide → 4-Propylpicolinonitrile

HRID 853992

반응식

HRID 853992 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 230032234-Propylpicolinonitrile수율 93%

시약·촉매·용매 1

HCID 11430Potassium Carbonate용매

실험 절차

To 4-propylpyridine (TCI) (2.5 g, 20 mmol), 30% hydrogen peroxide (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=n-Propyl) 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).

후처리

  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

출처 및 근거

ORD 기록
ord-bd81a32f44014ea5879d2e84b6aeba66
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256177B2

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