p-Fluoronitrobenzene → HCID 18677160, compound

HRID 1634092Notes

Reaction equation

[CH3:1][N:2]([CH3:12])[C:3]1[NH:7][N:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:4]=1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1)([O-:15])=[O:14]>>[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([N:7]2[C:3]([N:2]([CH3:12])[CH3:1])=[CH:4][C:5]([C:8]([F:11])([F:9])[F:10])=[N:6]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

Reactant 2

HCID 9590p-Fluoronitrobenzene

HCID 178482848HCID 178482848, compound

Product 1

HCID 18677160HCID 18677160, compound

Procedure

5-Dimethylamino-3-trifluoromethylpyrazole (2.9 mmol) was reacted with 4-nitrofluorobenzene (2.9 mmol), as described in Method L, to give 1-(4′-nitrophenyl)-5-dimethylamino-3-trifluoromethylpyrazole which was purified by chromatography over silica gel (hexanes/EtOAc, 8:2) (0.423 g, 46%). The nitrophenylpyrazole (1.35 mmol) was reduced by phase transfer hydrogenation, described generally in Method L, to give 1(4′-aminophenyl)-5-dimethylamino-3-trifluoromethylpyrazole as an off-white solid (0.321 g, 84%).

Sources & evidence

ORD record: ord-7bb43401ea8e45df8a68c2b78149d143
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506747B1

Reaction notes

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