Methyl iodide → N~2~-Methyl-4-nitrobenzene-1,2-diamine

HRID 1253816Notes

Reaction equation

HRID 1253816 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:11])[C:7]([NH2:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].CI.[C:14](=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:14][NH:11][C:6]1[C:7]([NH2:10])=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 21956374N~2~-Methyl-4-nitrobenzene-1,2-diamineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1 L round bottom flask was charged with 4-nitrobenzene-1,2-diamine (40 g, 0.26 mol), methyl iodide (13 ml, 0.21 mol) and DMF (300 ml), followed by the addition of saturated sodium carbonate (60 ml) over 2-3 minutes under rapid stirring. After stirring overnight at room temperature the reaction mixture was filtered and then concentrated in vacuo to a dark red oil. The residue was purified by flash column chromatography (15 to 30% ethyl acetate/petrol) to afford the title compound (27 g, 61% yield).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated in vacuo to a dark red oil
  3. customThe residue was purified by flash column chromatography (15 to 30% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-8c809b56cd724c6f8b5f3bc6ae1c03a8
Source dataset
uspto-grants-2013_06
Patent number
US08455507B2

Reaction notes

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