5'-Chloro-4'-methoxy-2'-nitroacetanilide → 5-Chloro-4-methoxy-2-nitroaniline

HRID 2064653Notes

Reaction equation

HRID 2064653 reaction equation
[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH:8]C(=O)C)[CH:7]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH2:8])[CH:7]=1

Participants

4

Reactant 2

HCID 27806535'-Chloro-4'-methoxy-2'-nitroacetanilideHCID 10942334Sodium Methoxide

Product 1

HCID 101043255-Chloro-4-methoxy-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(5-Chloro-4-methoxy-2-nitrophenyl)acetamide (8.0 g, Reference Example 32(i) was added to a solution of sodium methoxide (2.0 g, 0.037 mole) in methanol (150 mL) and the mixture was stirred at ambient temperature for 4 hours. The reaction mixture was added to ice water (750 mL), stirred for 15 minutes and the aqueous mixture was filtered. The precipitate was washed with water and dried at 60° C. under vacuum to give 5-chloro-4-methoxy-2-nitrophenylamine (6.52 g) as an orange solid, mp 128-129° C.

Workup

  1. stirringstirred for 15 minutes
  2. filtrationthe aqueous mixture was filtered
  3. washThe precipitate was washed with water
  4. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-ad1a5f12724344c987d1d124cbafeb24
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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