Sodium Nitrate → HCID 59518096, compound

HRID 1160874Notes

Reaction equation

HRID 1160874 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](N)[CH:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[N+]([O-])([O-])=[O:20].[Na+].F[P-](F)(F)(F)(F)F.[H+]>Cl.O>[CH3:1][C:2]1[CH:3]=[C:4]([OH:20])[CH:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 24268Sodium NitrateHCID 16211447Hexafluorophosphoric acidHCID 67153606HCID 67153606, compound

Product 1

HCID 59518096HCID 59518096, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
-15 °C

Procedure

5-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylamine (2.74 g, 10.87 mmol) is suspended in hydrochloric acid (21.74 mL, 5N) and the solution is cooled to −15° C. in a brine/ice bath. Sodium nitrate (0.9 g, 13.04 mmol) in water (10 mL) is added slowly to the mixture. The reaction is allowed to stir at −15° C. for ten minutes after complete addition. Hexafluorophosphoric acid (5 mL, 21.74 mmol of a 60% wt. solution in water) is added slowly to the mixture. The resulting slurry is filtered, rinsed with cold water, methanol, and diethyl ether, and dried under vacuum. This solid is added in small portions to a round bottom containing acetic acid (10 mL) at 105° C. This solution is cooled to room temperature then treated with sodium hydroxide (25 mL, 5N) for 30 min. The pH of this solution is adjusted to 6 with hydrochloric acid, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, then filtered and concentrated to provide the title product (2.2 g, 8.69 mmol).

Workup

  1. additionafter complete addition
  2. filtrationThe resulting slurry is filtered
  3. washrinsed with cold water, methanol, and diethyl ether
  4. customdried under vacuum
  5. additionThis solid is added in small portions to a round
  6. additionbottom containing acetic acid (10 mL) at 105° C
  7. temperatureThis solution is cooled to room temperature
  8. additionthen treated with sodium hydroxide (25 mL, 5N) for 30 min
  9. extractionextracted with ethyl acetate
  10. washwashed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-1ee35c58d5f246dfb571c2a7c3861401
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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