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

HRID 723740

반응식

HRID 723740 반응식
[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

참가 물질

4

반응물 1

HCID 2918672-Methoxy-4-nitrobenzonitrile

생성물 1

HCID 2327354-Amino-2-methoxybenzonitrile

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 22609514Ethyl acetate acetate용매

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온도
75 °C

실험 절차

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 additonal 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.

후처리

  1. customto give a clear solution
  2. stirringThe mixture was stirred at 75° C. for an additonal 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

출처 및 근거

ORD 기록
ord-f8f6c468e4314cbf9fd63528e3eb1541
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141578B2

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