2,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenyl → 2,6-Dimethyl-4'-(trifluoromethyl)biphenyl-4-amine

HRID 1427442Notes

Reaction equation

HRID 1427442 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 674856592,6-Dimethyl-4-nitro-4'-(trifluoromethyl)biphenylHCID 178418361HCID 178418361, compound

Product 1

HCID 674849042,6-Dimethyl-4'-(trifluoromethyl)biphenyl-4-amineYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2,6-dimethyl-4-nitro-4′-(trifluoromethyl)biphenyl (600 mg, 2.03 mmol) in ethanol (20 mL) was added 10 wt % palladium on carbon (18 mg). The reaction was pressurized to 50 psi hydrogen and stirred at room temperature overnight. The reaction was filtered onto Celite and concentrated. Purification by column chromatography gave 2,6-dimethyl-4′-(trifluoromethyl)biphenyl-4-amine (480 mg, 89%) as a light yellow solid. 1H NMR (400 MHz, CDCl3, δ): 7.65 (d, 2H), 7.27 (s, 1H), 7.25 (s, 1H), 6.48 (s, 2H), 3.80 (s, 2H), 1.94 (s, 6H). MS (M+1): 266.1.

Workup

  1. filtrationThe reaction was filtered onto Celite
  2. concentrationconcentrated
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-12171385c2314a82bd97618e2548ac21
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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