5-(Methylthio)-2-nitropyridine → 5-(Methylsulfanyl)pyridin-2-amine

HRID 22888ノート

反応式

HRID 22888 の反応式
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-])=O)=[N:7][CH:8]=1>C(O)(=O)C.Cl.[Zn]>[NH2:9][C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][N:7]=1

参加物

5

反応物 1

HCID 220361825-(Methylthio)-2-nitropyridine

生成物 1

HCID 151797975-(Methylsulfanyl)pyridin-2-amine収率 64%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒

実験手順

This nitropyridine (300 mg, 1.8 mmol) was dissolved in a mixed solvent of acetic acid (7 ml) and conc. hydrochloric acid (0.5 ml), and zinc (692 g, 10.6 mmol) was added thereto in small portions while being cooled with ice for 5 minutes. After the mixture was stirred for 30 minutes at the room temperature, the reaction mixture was filtered, and the filtrate was neutralized with an aqueous solution of sodium hydrogencarbonate, and extracted with methylene chloride. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Thereafter, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (eluent-hexane:ethyl acetate=1:1→chloroform:methanol=20:1) to obtain 158 mg (yield 64%) of 2-amino-5-methylthiopyridine as a pale-yellow powdery crystal.

後処理

  1. additionwas added
  2. temperaturein small portions while being cooled with ice for 5 minutes
  3. filtrationthe reaction mixture was filtered
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
  7. distillationThereafter, the solvent was distilled off
  8. customthe resulting crude product was purified through silica gel chromatography (eluent-hexane:ethyl acetate=1:1→chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-038f738afc43404da30a0394b7d47f63
出典データセット
uspto-grants-2005_02
特許番号
US06849647B1

反応ノート

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