Potassium Carbonate → N-Cyclopropyl-5-fluoro-2-nitroaniline

HRID 1048943Notes

Reaction equation

HRID 1048943 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+].[CH:20]1([NH2:23])[CH2:22][CH2:21]1>ClCCl>[CH:20]1([NH:23][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 69828CyclopropylamineHCID 522689Potassium Fluoride

Product 1

HCID 53621866N-Cyclopropyl-5-fluoro-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 cyclopropylamine (0.52 mL, 7.54 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: LCMS m/z 196.95 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.20 (dd, J=9.5, 6.0 Hz, 2 H), 6.95 (dd, J=11.4, 2.6 Hz, 1 H), 6.43-6.39 (m, 1 H), 2.58-2.53 (m, 1 H), 0.96-0.92 (m, 2 H), 0.69-0.66 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-6043d29bff0f4680a0c301cad6c68cf0
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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