Methyl iodide → 6-Nitro-o-anisidine

HRID 1594524Notes

Reaction equation

HRID 1594524 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 854916-Nitro-o-anisidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To acetone (60 mL) charged with 2-amino-3-nitrophenol (32 mmol, 4.9 g) and K2CO3 (48 mmol, 6.62 g) was added MeI (32 mmol, 1.98 mL). The reaction mixture was stirred rapidly at ambient temperature for 16 h. Acetone was removed under reduced pressure and the residue was partitioned between CH2Cl2 and brine. The organic phase was dried over MgSO4 and concentrated under reduced pressure to provide the product as a brown solid. LC-MS (ESI, Method C) 2.56 min, m/z 169.1 (M+1).

Workup

  1. customAcetone was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05c995fc90e04825b37e66d7b819f84f
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

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