2-Chloro-3-methyl-5-nitropyridine → 6-Chloro-5-methylpyridin-3-amine

HRID 367065

反応式

HRID 367065 の反応式
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>O.CC(O)=O.[Fe]>[NH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Cl:1])=[N:3][CH:4]=1

参加物

4

反応物 1

HCID 896482-Chloro-3-methyl-5-nitropyridine

生成物 1

HCID 122956076-Chloro-5-methylpyridin-3-amine収率 89%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 21899381Acetic acid--water (1/1)溶媒

実験手順

2-Chloro-3-methyl-5-nitropyridine (3.2 g, 18.5 mmol; Maybridge Chemical Co.) was dissolved in a mechanically stirred solution of H2O/HOAc (60 mL, 5:1). Iron powder was added over a 5 h period, maintaining the temperature below 40° C., and stirring was continued until starting material had be consumed. The reaction mixture was filtered, and the filter cake was washed with EtOAc. The aqueous filtrate was extracted with EtOAc, and the combined organic fractions were washed with saturated NaHCO3 solution, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; CHCl3 /MeOH, 98:2) to afford 5-amino-2-chloro-3-methylpyridine as an orange solid (2.34 g, 89%): MS (CI/NH3) m/z: 143 (M+H)+ ; NMR (DMSO-d6, 300 MHz) δ 2.17 (s, 3H), 5.40 (br s, 2H), 6.90 (d, J=2.2 Hz, 1H), 7.54 (d, J=2.2 Hz, 1H).

後処理

  1. temperaturemaintaining the temperature below 40° C.
  2. customhad be consumed
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake was washed with EtOAc
  5. extractionThe aqueous filtrate was extracted with EtOAc
  6. washthe combined organic fractions were washed with saturated NaHCO3 solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was chromatographed (silica gel; CHCl3 /MeOH, 98:2)

出典と根拠

ORDレコード
ord-08df4e70870c43d5bdb28521a8e5eee0
出典データセット
uspto-grants-2000_10
特許番号
US06133253

関連ノート

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