Methylamine → N3-Methyl-3',4-dinitrobiphenyl-3,4'-diamine

HRID 628575Notes

Reaction equation

HRID 628575 reaction equation
F[C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C([O-])([O-])=O.[K+].[K+].[CH3:27][NH2:28]>C(Cl)Cl>[CH3:27][NH:28][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 86661419HCID 86661419, compound

Product 1

HCID 86661420N3-Methyl-3',4-dinitrobiphenyl-3,4'-diamineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3′-Fluoro-3,4′-dinitrobiphenyl-4-amine (285 mg, 1.03 mmol) was suspended in DCM (10 mL). K2CO3 (284 mg, 2.06 mmol) was added, followed by MeNH2 (40% in H2O, 10 mL). The mixture was stirred at room temperature for 72 h. The solution was then washed with H2O and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford the product as a red solid (296 mg, 100%).

Workup

  1. washThe solution was then washed with H2O and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d1eedf48f8646be90c1c67460cd2feb
Source dataset
uspto-grants-2016_04
Patent number
US09314456B2

Reaction notes

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