Piconol → HCID 18357727、化合物

HRID 427733ノート

反応式

HRID 427733 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[C:17]([CH3:18])=[CH:16][C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1>CN(C)C=O>[CH3:18][C:17]1[C:12]([O:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:13][CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=1

参加物

5

反応物 3

HCID 11474PiconolHCID 24758Sodium hydrideHCID 896482-Chloro-3-methyl-5-nitropyridine

生成物 1

HCID 18357727HCID 18357727、化合物収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-20 °C

実験手順

2-Pyridylcarbinol (1.96 g, 18 mmol) in dry dimethylformamide (20 ml) was cooled to −20° C. and treated with sodium hydride (0.48 g of 80% dispersion in mineral oil, 16 mmol). The mixture was stirred under argon at −20° C. for one hour then a solution of 2-chloro-3-methyl-5-nitropyridine (2.07 g, 12 mmol) in dry dimethylformamide (10 ml) was added and the mixture was allowed to warn to room temperature over 16 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane (3×100 ml) and 10% aqueous sodium hydroxide solution(75 ml). The combined organics were dried (Na2SO4) and evaporated in vacuo to a residue which was subjected to flash column chromatography with 1:1 ethyl acetate/petroleum ether as eluant to afford the title compound (1.47 g, 51%) as lemon yellow crystals.

後処理

  1. waitto warn to room temperature over 16 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between dichloromethane (3×100 ml) and 10% aqueous sodium hydroxide solution(75 ml)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. customevaporated in vacuo to a residue which

出典と根拠

ORDレコード
ord-1bb25614cbb04cd19954d7e973d0c41c
出典データセット
uspto-grants-2001_11
特許番号
US06313145B1

反応ノート

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