Water → 5-fluoro-N-methyl-2-nitroaniline

HRID 1048936Notes

Reaction equation

HRID 1048936 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH3:20][NH2:21].O>ClCCl>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=1)[NH:21][CH3:20]

Participants

7

Reactant 5

HCID 962WaterHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 229057745-fluoro-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

2,4-Difluoronitrobenzene (1.00 g, 6.29 mmol), potassium fluoride (0.365 g, 6.29 mmol), potassium carbonate (0.869 g, 6.29 mmol), and 40% methylamine in water (0.58 mL, 7.5 mmol) were added to a vial and heated in a microwave at 90° C. for 10 min. The reaction was then diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate, and concentrated to provide the title compound: 1H NMR (500 MHz, CDCl3) δ 8.22 (dd, J=9.4, 6.1 Hz, 1 H), 8.16 (br s, 1 H), 6.48 (dd, J=11.5, 2.6 Hz, 1 H), 6.40-6.36 (m, 1 H), 3.01 (d, J=5.0 Hz, 3 H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-59b8956cd2634c9eb9f7b449a76c4cba
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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