Pyridine → 4-(2-Trifluoromethyl-pyridin-4-ylmethyl)-phenylamine

HRID 2244151Notes

Reaction equation

HRID 2244151 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.N1C=CC=CC=1>C(O)C.[Pd]>[F:18][C:15]([F:16])([F:17])[C:11]1[CH:10]=[C:9]([CH2:8][C:7]2[CH:19]=[CH:20][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 578333894-(4-Nitrobenzyl)-2-(trifluoromethyl)pyridine

Product 1

HCID 578335204-(2-Trifluoromethyl-pyridin-4-ylmethyl)-phenylamineYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

10% Degussa Pd on carbon (15 mg, 0.4 mmol) was flushed with nitrogen then diluted in ethanol (2 mL). A solution of 4-(4-nitrobenzyl)-2-(trifluoromethyl)pyridine (100 mg, 0.35 mmol) in ethanol (2 mL) and pyridine (14 mg, 0.18 mmol) was subsequently added, and the mixture was flushed again with nitrogen prior to placing a hydrogen balloon on the flask. The mixture was stirred at rt overnight then filtered through Celite® and concentrated. The residue was dissolved in ethyl acetate and filtered through a silica gel plug, eluting with 50-100% ethyl acetate in hexanes, to give 4-(2-trifluoromethyl-pyridin-4-ylmethyl)-phenylamine as a clear colorless oil (76 mg, 85%). 1H NMR (CHCl3-d) δ 8.57 (d, J=5.0 Hz, 1H), 7.47 (s, 1H), 7.26 (m, 1H), 6.93 (m, 2H), 6.65 (m, 2H), 3.92 (s, 2H), 3.57 (br s, 2H).

Workup

  1. customthe mixture was flushed again with nitrogen
  2. filtrationthen filtered through Celite®
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. filtrationfiltered through a silica gel plug
  6. washeluting with 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-941b7fd5ea5f4139ae9f6509a189befa
Source dataset
uspto-grants-2010_03
Patent number
US07678804B2

Reaction notes

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