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

HRID 1441880

Reaction equation

HRID 1441880 reaction equation
[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

Participants

4

Reactant 1

HCID 2918672-Methoxy-4-nitrobenzonitrile

Product 1

HCID 2327354-Amino-2-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 22609514Ethyl acetate acetateSolvent

Conditions

Temperature
75 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d44409223a8d4490a9b4b3f617f0f9f6
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Linked notes

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