2-Methoxy-4-nitrobenzonitrile → 4-Amino-2-methoxybenzonitrile

HRID 2110503

反応式

HRID 2110503 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]>[Fe].CC(O)=O.CCOC(C)=O>[NH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1

参加物

4

反応物 1

HCID 2918672-Methoxy-4-nitrobenzonitrile

生成物 1

HCID 2327354-Amino-2-methoxybenzonitrile

試薬・触媒・溶媒 2

HCID 23925Iron触媒2 回HCID 22609514Ethyl acetate acetate溶媒

反応条件

温度
75 °C

実験手順

2-Methoxy-4-nitro-benzonitrile (500 mg, 2.81 mmol) was suspended into 4 mL AcOH/EtOAc (1:1) and the resulting mixture was heated to 75° C. to give a clear solution. Fe powder (313 mg, 5.61 mmol, 325 Mesh) was added and the mixture was stirred for 30 min, after which additional Fe powder (313 mg, 5.61 mmol, 325 Mesh) was introduced. The mixture was stirred at 75° C. for an additional 30 min, and then cooled to rt and filtered, eluting with EtOAc. The filtrate was concentrated in vacuo, re-dissolved in EtOAc, filtered (eluting with EtOAc) and concentrated. Purification was achieved by silica gel flash chromatography with 0 to 10% MeOH in CH2Cl2 to give compound 848A as a tan solid.

後処理

  1. customto give a clear solution
  2. stirringThe mixture was stirred at 75° C. for an additional 30 min
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. washeluting with EtOAc
  6. concentrationThe filtrate was concentrated in vacuo
  7. dissolutionre-dissolved in EtOAc
  8. filtrationfiltered
  9. wash(eluting with EtOAc)
  10. concentrationconcentrated
  11. customPurification

出典と根拠

ORDレコード
ord-df22aa894c0a47e88495e10cc4b34e6f
出典データセット
uspto-grants-2009_04
特許番号
US07517904B2

関連ノート

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