HCID 10608727, compound → HCID 22025336, compound

HRID 1792834Notes

Reaction equation

HRID 1792834 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[C:4]([N+:10]([O-])=O)[C:3]=1[O:13][CH3:14]>CO>[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([NH2:10])[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 1

HCID 10608727HCID 10608727, compound

Product 1

HCID 22025336HCID 22025336, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-Chloro-2-methoxy-4,5-dimethyl-3-nitro-benzene (10.0 g, 46.4 mmol; Stachel et. al., J. Org. Chem. 1997, 46, 4756) is dissolved in MeOH (200 mL) in a 500 mL round bottom flask. The flask is purged with N2 and 10% Pd on Carbon (0.7 g) is added and the reaction is again purged with N2. The reaction is purged with H2 and rapidly stirred for 15 h. The major product is the desired product from partial reduction. The reaction is filtered on celite and washed with MeOH and concentrated. Overreduction (des-chloro) product is filtered off as a solid from partially dissolving the crude reaction mixture in EtOH and MeOH to provide 3-chloro-2-methoxy-5,6-dimethyl-phenylamine which is used without further purification.

Workup

  1. customThe flask is purged with N2 and 10% Pd on Carbon (0.7 g)
  2. additionis added
  3. customthe reaction is again purged with N2
  4. customThe reaction is purged with H2
  5. filtrationThe reaction is filtered on celite
  6. washwashed with MeOH
  7. concentrationconcentrated
  8. filtrationOverreduction (des-chloro) product is filtered off as a solid
  9. dissolutionfrom partially dissolving the crude
  10. customreaction mixture in EtOH

Sources & evidence

ORD record
ord-bfe19503fdc247b9865afff196382cda
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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