Hydrogen Peroxide → 4-Propylpicolinonitrile

HRID 853992

反応式

HRID 853992 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 230032234-Propylpicolinonitrile収率 93%

試薬・触媒・溶媒 1

HCID 11430Potassium Carbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bd81a32f44014ea5879d2e84b6aeba66
出典データセット
uspto-grants-2007_08
特許番号
US07256177B2

関連ノート

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