Water → 2-Chloro-5-methoxy-3-methylpyridine

HRID 1065233

反応式

HRID 1065233 の反応式
[H-].[Na+].[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[CH:6][N:5]=1.[CH3:12]I.O>CN(C=O)C>[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][N:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128520156-Chloro-5-methylpyridin-3-ol

生成物 1

HCID 128520162-Chloro-5-methoxy-3-methylpyridine収率 101.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Into a flame dried flask under N2 was placed DMF (150 mL), NaH (50% oil dispersion, 4.0 g, 0.08 mol) and 2-chloro-5-hydroxy-3-methylpyridine (11.7 g, 0.08 mol). The solution was stirred at 0°-5° C. until the evolution of H2 ceased and then a solution of CH3I (5.6 mL, 0.09 mol) in DMF (50 mL) was added dropwise. After the addition, the solution was allowed to stir at room temperature overnight. The resulting slurry was added to H2O and extracted with Et2 0 (3×). The organic layer was concentrated and the residue distilled at 85° C. (0.6 mm) to yield 12.8 g of 2-chloro-5-methoxy-3-methylpyridine (95%) as an oil; 1H NMR (CDCl3) δ2.35 (3H, s), 3.8 (3H, s), 7.1 (1H, d, J=3) and 7.9 (1H, d, J=3); MS m/e (M+) 157.

後処理

  1. customInto a flame dried flask under N2
  2. additionAfter the addition
  3. stirringto stir at room temperature overnight
  4. extractionextracted with Et2 0 (3×)
  5. concentrationThe organic layer was concentrated
  6. distillationthe residue distilled at 85° C. (0.6 mm)

出典と根拠

ORDレコード
ord-dc38a81a69b14da9adb9c1f247a071de
出典データセット
uspto-grants-1982_05
特許番号
US04329351

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