Nitric Acid → HCID 86223897, compound

HRID 2387015Notes

Reaction equation

HRID 2387015 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([F:14])([F:13])[F:12])[N+:5]=1[O-:15].[N+:18]([O-])([OH:20])=[O:19].[OH-].[Na+]>OS(O)(=O)=O>[N+:18]([C:8]1[CH:7]=[C:6]([CH2:10][C:11]([F:14])([F:12])[F:13])[N+:5]([O-:15])=[C:4]([CH2:3][C:2]([F:1])([F:16])[F:17])[CH:9]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 86223896HCID 86223896, compound

Product 1

HCID 86223897HCID 86223897, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

2,6-Bis-(2,2,2-trifluoro-ethyl)-pyridine 1-oxide (2.65 g, 10.22 mmol)was dissolved in H2SO4 (4 mL) and cooled to 0° C. HNO3 (3.2 mL) was added slowly and after the addition was complete the reaction mixture was heated to 90° C. for 2 hours. The mixture was poured into ice, made basic with 15% NaOH and extracted with CH2Cl2. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a red oil (2.72 g, 81%). 1H NMR (400 MHz, CDCl3): δ 3.95 (t, J=10.1 Hz, 4 H), 8.31 (s, 2 H).

Workup

  1. additionafter the addition
  2. temperaturewas heated to 90° C. for 2 hours
  3. additionThe mixture was poured into ice
  4. extractionextracted with CH2Cl2
  5. washThe organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to a red oil (2.72 g, 81%)

Sources & evidence

ORD record
ord-aec2e2c15775466d8c720131df274737
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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