Ammonium Hydroxide → 4-Amino-3-methylbenzonitrile

HRID 276241

반응식

HRID 276241 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 70103164-Amino-3-methylbenzonitrile수율 92%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-44cc49bea78a4a69bac44e5def73b036
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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