Ammonium formate → 5-Amino-2-(2-methylpropyl)benzonitrile

HRID 1942630

反応式

HRID 1942630 の反応式
[CH3:1][CH:2]([CH3:15])[CH2:3][C:4]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:5]=1[C:6]#[N:7].C([O-])=O.[NH4+]>CO.O.[Zn]>[NH2:12][C:9]1[CH:10]=[CH:11][C:4]([CH2:3][CH:2]([CH3:15])[CH3:1])=[C:5]([CH:8]=1)[C:6]#[N:7]

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 222280302-Isobutyl-5-nitrobenzonitrile

生成物 1

HCID 222279325-Amino-2-(2-methylpropyl)benzonitrile収率 273.5%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-isobutyl-5-nitrobenzonitrile (D56) (7.5 g) in methanol (80 mL) and water (80 mL) was added ammonium formate (51.9 g) and zinc (26.9 g). The reaction mixture was stirred at 80° C. for 4 h. After cooling the reaction, the solid was filtered, the filtrate was concentrated under reduced pressure, the residue was extracted with EtOAc (300 mL*2), the combined organic layers were washed with water (30 mL*2), dried and concentrated to give 5-amino-2-(2-methylpropyl)benzonitrile (D57) (17.5 g) as a colorless solid. MS (ES): C11H14N2 requires 174. found 175.1 (M+H+).

後処理

  1. temperatureAfter cooling
  2. customthe reaction
  3. filtrationthe solid was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionthe residue was extracted with EtOAc (300 mL*2)
  6. washthe combined organic layers were washed with water (30 mL*2)
  7. customdried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-f236859ad9a142ca9223828c6a1e47f7
出典データセット
uspto-grants-2013_03
特許番号
US08389508B2

関連ノート

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