N-cyclopropyl-4,5-difluoro-2-nitroaniline → N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine

HRID 1048953Notes

Reaction equation

HRID 1048953 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=2[N+:13]([O-])=O)[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([NH:4][C:5]2[C:6]([NH2:13])=[CH:7][C:8]([F:12])=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

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

Product 1

HCID 68053726N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the title compound from Step A (1.22 g, 5.69 mmol) were added 10% palladium on carbon (0.122 g, 1.15 mmol) and methanol (28.5 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The mixture was then filtered through CELITE® using dichloromethane, and the filtrate was concentrated. Purification by flash chromatography on silica gel (0-30% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.83 (dd, J=12.4, 7.9 Hz, 1 H), 6.51 (dd, J=11.3, 7.8 Hz, 1 H), 3.82 (br s, 1 H), 3.15 (br s, 2 H), 2.40-2.37 (m, 1 H), 0.77-0.73 (m, 2 H), 0.52-0.50 (m, 2 H).

Workup

  1. filtrationThe mixture was then filtered through CELITE®
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromatography on silica gel (0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d9f95678cdfc4c0f9b7b20912fcc376d
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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