Ammonium Chloride → 2-Chloro-6-methylpyridin-4-amine

HRID 2192996ノート

反応式

HRID 2192996 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[N+:3]=1[O-].[NH4+].[Cl-]>CCO.O.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:11])[N:3]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 27518132-Chloro-6-methyl-4-nitropyridin-N-oxide

生成物 1

HCID 126437072-Chloro-6-methylpyridin-4-amine

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

A solution of 2-chloro-6-methyl-4-nitropyridine 1-oxide (52 g, 0.27 mol) in EtOH and H2O was treated with powdered iron (46 g, 0.83 mol) and NH4Cl (44 g, 0.83 mol). The mixture was stirred at 90° C. for 3 h. After cooling to room temperature the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine (500 mL), dried over magnesium sulfate, filtered and concentrated to afford 2-chloro-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3) δ 6.36 (d, J=1.5 Hz, 1H), 6.28 (d, J=1.2 Hz, 1H), 4.30 (m, 2H), 2.34 (s, 3H). LRMS calc'd for (C6H7ClN2) [M+H]+, 143; found 143.

後処理

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. filtrationwas filtered
  3. extractionthe filtrate was extracted with ethyl acetate (3×500 mL)
  4. washThe combined organic layers were washed with brine (500 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fb488526fb5447b1a3921d3a75903644
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

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