2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-Phenyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

HRID 871538Notes

Reaction equation

HRID 871538 reaction equation
[C:1]1([N:7]2[CH:11]([C:12]([F:15])([F:14])[F:13])[CH2:10][C:9]([NH2:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[C:1]1([N:7]2[C:11]([C:12]([F:15])([F:13])[F:14])=[CH:10][C:9]([NH2:16])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 671593011-phenyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-3-amine

Product 1

HCID 534033781-Phenyl-5-(trifluoromethyl)-1H-pyrazol-3-amineYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-phenyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-3-amine (1.47 g, 6.41 mmol) and DDQ (1.748 g, 7.7 mmol) in CH2Cl2 (30 mL) was stirred at room temperature for 4 hours. The crude product was purified by silica gel chromatography twice (with 15-35% and 10-30% EtOAc/hexane as eluants) to afford 1-phenyl-5-(trifluoromethyl)-1H-pyrazol-3-amine as an oil (0.666 g, 46%). 1H NMR (300 MHz, CDCl3) δ 7.42 (m, 5H), 6.18 (s, 1H), 3.82 (br, 2H); LC-MS (ESI) m/z 228 (M+H)+.

Workup

  1. customThe crude product was purified by silica gel chromatography twice (with 15-35% and 10-30% EtOAc/hexane as eluants)

Sources & evidence

ORD record
ord-b947d25937b04343962dae9a29f1cb22
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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