Stannous Chloride → 4-Amino-3-methylbenzonitrile

HRID 2753

反応式

HRID 2753 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6].Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO.CCOC(C)=O>[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1]

参加物

6

反応物 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 28014343-Methyl-4-nitrobenzonitrile

生成物 1

HCID 70103164-Amino-3-methylbenzonitrile収率 70.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.3 mmol) in 100 mL of EtOH is added SnCl2 (13.9 g, 61.7 mmol). The resulting solution is heated at reflux. After 2 h, the solution is cooled to ambient temperatures. The solution is poured into 150 mL of ice water. The pH of the solution is adjusted to >7 with a solution of saturated NaHCO3. The solution is diluted with EtOAc and the resulting mixture is filtered through Celite. The filtered solution is separated. The organic layer is dried over MgSO4, filtered and concentrated to give the title compound (1.57 g, 8.7 mmol) as an off-white solid.

後処理

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux
  3. temperaturethe solution is cooled to ambient temperatures
  4. filtrationthe resulting mixture is filtered through Celite
  5. customThe filtered solution is separated
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-68a8e77da56c464fb8e4488b01b277d1
出典データセット
uspto-grants-1998_03
特許番号
US05731315

関連ノート

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