Potassium Carbonate → N-cyclopropyl-4,5-difluoro-2-nitroaniline

HRID 1048952Notes

Reaction equation

HRID 1048952 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH:21]1([NH2:24])[CH2:23][CH2:22]1>ClCCl>[CH:21]1([NH:24][C:2]2[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 86703086N-cyclopropyl-4,5-difluoro-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

2,4,5-Trifluoronitrobenzene (2.00 g, 11.3 mmol), potassium fluoride (0.656 g, 11.3 mmol), potassium carbonate (1.561 g, 11.29 mmol), and cyclopropylamine (0.93 ml, 13.55 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 under reduced pressure. Purification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 8.04 (dd, J=10.4, 8.5 Hz, 1 H), 7.09 (dd, J=12.6, 7.0 Hz, 1 H), 2.55-2.54 (m, 1 H), 0.97-0.93 (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 under reduced pressure
  4. customPurification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e38663c16df94e1e8524b7f57fc221d4
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

Loading…