Triethylamine → 5-(Trifluoromethyl)pyridin-3-amine

HRID 1098577Notes

Reaction equation

HRID 1098577 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][C:12]([C:18]([F:21])([F:20])[F:19])=[CH:11][N:10]=1>[Pd].C(O)C>[F:21][C:18]([F:19])([F:20])[C:12]1[CH:13]=[C:14]([NH2:15])[CH:9]=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Product 1

HCID 140519365-(Trifluoromethyl)pyridin-3-amineYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A Parr hydrogenation flask was charged with 10% Palladium on carbon, 50% wet (0.050 g, 0.023 mmol) and ethanol (10 mL). Triethylamine (1.0 ml, 3.09 mmol), 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (0.70 g, 3.09 mmol) and an additional 10 mL of ethanol were added. The flask was purged of air, charged with 48 psi of hydrogen, and shaken for 6 h. The reaction mixture was purged of hydrogen in vacuo and filtered through Celite®, washing with EtOAc (20 mL) and EtOH (20 mL). The filtrate was concentrated in vacuo and the product partitioned between EtOAc (40 mL) and water (20 mL). The organics were washed with sat aq NaHCO3 (20 mL) and brine (20 mL), dried (MgSO4) and concentrated in vacuo to provide 5-(trifluoromethyl)pyridin-3-amine (498 mg, 99% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.14 (m, 1 H), 8.00 (s, 1 H), 7.13 (m, 1 H), 5.84 (s, 2 H); MS (ESI) m/z 163.0 (M+H+).

Workup

  1. customThe flask was purged of air
  2. additioncharged with 48 psi of hydrogen
  3. customThe reaction mixture was purged of hydrogen in vacuo
  4. filtrationfiltered through Celite®
  5. washwashing with EtOAc (20 mL) and EtOH (20 mL)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe product partitioned between EtOAc (40 mL) and water (20 mL)
  8. washThe organics were washed with sat aq NaHCO3 (20 mL) and brine (20 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ce2f05ac1454210a79422e31f6f3fc3
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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