Potassium Hydroxide → 4-(4-Methyl-1h-imidazol-1-yl)benzenamine

HRID 472160

反応式

HRID 472160 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH:6]=1.O.O.Cl[Sn]Cl.[OH-].[K+]>C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:6]=1

参加物

5

反応物 3

HCID 14797Potassium Hydroxide2 回HCID 61436Stannous chloride dihydrateHCID 160051694-Methyl-1-(4-nitrophenyl)-1H-imidazole

生成物 1

HCID 160051704-(4-Methyl-1h-imidazol-1-yl)benzenamine収率 10,152.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

4-(4-methyl-1H-imidazol-1-yl)nitrobenzene (22.5 g; 0.87 mmol) is dissolved in abs. ethanol (250 mL), then SnCl2.2H2O (125 g; 0.55 mol) is added portion-wise, on cooling at 0° C. The resulting mixture is stirred at r.t. for 2 hours and heated at reflux overnight. The reaction mixture is then cooled at r.t. and the pH is adjusted to 12, by adding 30% KOH (500 mL), then KOH pellets under stirring. The resulting suspension is filtered and the cake is washed with ethanol, the combined filtrate and washings are concentrated and the residue is extracted with DCM. Concentration of the combined organic extracts afforded the title product as a slight brown solid (15.3 g; 80%), m.p.: 122-125° C. C10H11N3, MW 173.22.

後処理

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture is then cooled at r.t.
  4. filtrationThe resulting suspension is filtered
  5. washthe cake is washed with ethanol
  6. concentrationthe combined filtrate and washings are concentrated
  7. extractionthe residue is extracted with DCM

出典と根拠

ORDレコード
ord-38007aa131cc43e6ac40724e0553f5da
出典データセット
uspto-grants-2014_01
特許番号
US08633208B2

関連ノート

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