Sodium Hydroxide → 2-Amino-3-(trifluoromethyl)pyridine

HRID 269017Notes

Reaction equation

HRID 269017 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=CC=1.[OH-].[Na+]>OS(O)(=O)=O>[F:18][C:15]([F:16])([F:17])[C:14]1[C:9]([NH2:8])=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 29558569(4-Methoxy-benzyl)-(3-trifluoromethyl-pyridin-2-yl)-amine

Product 1

HCID 27609202-Amino-3-(trifluoromethyl)pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To conc. H2SO4 (230 mL) at 5° C. was dropwise added (4-methoxy-benzyl)-(3-trifluoromethyl-pyridin-2-yl)-amine (83.76 g, 297 mmol) keeping the internal temperature below 20° C. Stirring was continued at 23° C. for 30 min, poured onto ice, made alkaline with 32% NaOH-sol. (ca. 800 mL) [external ice cooling necessary!!!], saturated with solid NaCl, extracted twice with THF/TBME/DCM, dried over Na2SO4. Removal of the solvent in vacuum gave the product as a white solid (44.27 g, 92%). MS (ISP) 163.2 [(M+H)+].

Workup

  1. customat 5° C.
  2. customthe internal temperature below 20° C
  3. additionpoured onto ice
  4. extraction(ca. 800 mL) [external ice cooling necessary!!!], saturated with solid NaCl, extracted twice with THF/TBME/DCM
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-dd493dbc953f4b8eb6992d8b8d36dce7
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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