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

HRID 2173798Notes

Reaction equation

HRID 2173798 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-95f31ef0c0a64bde88be4e375fdb04bb
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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