Ammonium Chloride → 2-Methyl-6-(methylsulfonyl)pyridin-3-amine

HRID 1811598ノート

反応式

HRID 1811598 の反応式
[Cl-].[NH4+].[CH3:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])[N:5]=1>C(OCC)(=O)C.[Zn]>[CH3:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])[N:5]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 124082046-Methanesulfonyl-2-methyl-3-nitropyridine

生成物 1

HCID 510505272-Methyl-6-(methylsulfonyl)pyridin-3-amine収率 46.5%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of zinc dust (146 g, 2.01 mol) and aqueous ammonium chloride solution (3 M, 800 ml) was added dropwise a solution of 2-methyl-6-(methylsulfonyl)-3-nitropyridine (87.0 g, 401 mmol) in ethyl acetate (500 mL) via an addition funnel at 0° C. The mixture was stirred at room temperature for 17 h and filtered through Celite™. The filtrate was then extracted with ethyl acetate. The organic phase was separated, dried over MgSO4, filtered, and concentrated. The residue was recrystallized from ethanol to give the title compound (34.7 g, 46%) as a solid. Exact mass calculated for C7H10N2O2S: 186.1. Found: LCMS m/z=187.2 (M+H+).

後処理

  1. filtrationfiltered through Celite™
  2. extractionThe filtrate was then extracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-d43c28ee7a2045518a3645926f4aecae
出典データセット
uspto-grants-2013_01
特許番号
US08362248B2

反応ノート

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