Methyl iodide → (2-Bromo-3-methoxy-6-nitro-phenyl)-phenylamine

HRID 243074Notes

Reaction equation

HRID 243074 reaction equation
[Br:1][C:2]1[C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[OH:18].CI.[C:21](=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[Br:1][C:2]1[C:3]([O:18][CH3:21])=[CH:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68157225HCID 68157225, compound

Product 1

HCID 68157845(2-Bromo-3-methoxy-6-nitro-phenyl)-phenylamineYield 100.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-bromo-4-nitro-3-phenylaminophenol (450 mg, 1.45 mmol) in acetone was added methyl iodide (0.34 mL, 5.44 mmol) and potassium carbonate (751 mg, 5.44 mmol) and the reaction mixture heated at 40° C. for 16 h. The mixture was diluted with water and extracted with EtOAc (3×20 mL). The combined organic fractions were washed with brine, dried (MgSO4), concentrated in vacuo to give the title compound as a yellow oil (470 mg, 100%). 1H NMR 400 MHz δ (CDCl3): 8.36 (1H, br s), 8.19 (1H, d, J=9.6 Hz), 7.28-7.22 (2H, m), 7.05-7.00 (1H, m), 6.89-6.84 (2H, m), 6.69 (1H, d, J=9.7 Hz), 4.01 (3H, s).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62755d4a8bf84a67bbdd601314f13451
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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