Nitric Acid → HCID 13773044, compound

HRID 2291670Notes

Reaction equation

HRID 2291670 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[F:12][C:8]1[C:9]([N+:1]([O-:4])=[O:2])=[CH:10][CH:11]=[C:6]([F:5])[C:7]=1[C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 10899450HCID 10899450, compound

Product 1

HCID 13773044HCID 13773044, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of cold (0° C.) concentrated nitric acid (20.4 ml) and concentrated sulfuric acid (20.4 ml) was added in portions to a stirred solution of 10 g 4-(2,6-difluorophenyl)-pyridine in 56 ml concentrated sulfuric acid at 0° C. After 45 minutes at 0° C., the mixture was poured onto ice and the resulting solution was neutralized with solid sodium bicarbonate. The neutralized solution was then extracted twice with ethyl acetate and the organic extracts were dried and evaporated to give the product as a white solid of m p. 110°-112° C. (10.9 g, 88% yield). NMR (CDC13, 60 MHz): 8.8 (m, 2H), 8.2 (m, 1H), 7.0-7.6 (m, 3H).

Workup

  1. additionthe mixture was poured onto ice
  2. extractionThe neutralized solution was then extracted twice with ethyl acetate
  3. customthe organic extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-43af5b303a624232906ed019499d0162
Source dataset
uspto-grants-1989_01
Patent number
US04797490

Reaction notes

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