Methyl iodide → 6-Nitro-o-anisidine

HRID 33386

Reaction equation

HRID 33386 reaction equation
[OH-].[K+].[NH2:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:13].I[CH3:15]>CN(C=O)C>[CH3:15][O:13][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=1[NH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 854916-Nitro-o-anisidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

85% potassium hydroxide solution (11.7 g, 0.179 mol) is added to a solution of 25 g (0.162 mol) 2-amino-3-nitro-phenol in 200 mL DMF. Then 11.1 mL (0.178 mol) iodomethane are added dropwise and the mixture is stirred overnight at ambient temperature. The reaction mixture is poured onto ice and stirred for one hour. The precipitated product is filtered off, washed with water and dried.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. stirringstirred for one hour
  3. filtrationThe precipitated product is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-256aa94f9e5847479f45c40f7a09c03e
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Linked notes

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