Ammonium Hydroxide → 4-Amino-3-methylbenzonitrile

HRID 276241

反応式

HRID 276241 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.[NH4+].[OH-]>C(O)(=O)C.Cl>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([NH2:10])=[C:2]([CH3:1])[CH:3]=1)#[N:6]

参加物

6

反応物 3

HCID 14923Ammonium HydroxideHCID 24479Stannous ChlorideHCID 28014343-Methyl-4-nitrobenzonitrile

生成物 1

HCID 70103164-Amino-3-methylbenzonitrile収率 92%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒

実験手順

4-Cyano-2-methylaniline was synthesized as previously described (J. Med. Chem. (1991), 34, 3295): To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.34 mmol) in acetic acid (20 L) was added dropwise a solution of SnCl2 (9.6 g, 49.38 mmol) in conc. HCl (20 mL). After stirring for 3 h, the mixture was added carefully to a saturated NH4OH solution (120 mL) at 0° C. The resulting mixture was extracted with EtOAc (4×30 mL). The combined organic layers were sequentially washed with H2O (30 mL) and a saturated NaCl solution (30 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (10% EtOAc/hex) to give 4-cyano-2-methylaniline as a white solid (1.48 g, 92%): TLC (30% EtOAc in hexane) Rf0.23. This material was used without further purification.

後処理

  1. custom4-Cyano-2-methylaniline was synthesized
  2. extractionThe resulting mixture was extracted with EtOAc (4×30 mL)
  3. washThe combined organic layers were sequentially washed with H2O (30 mL)
  4. dry with materiala saturated NaCl solution (30 mL), dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (10% EtOAc/hex)

出典と根拠

ORDレコード
ord-44cc49bea78a4a69bac44e5def73b036
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

関連ノート

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