Nitric Acid → HCID 178468361, compound

HRID 1407072Notes

Reaction equation

HRID 1407072 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:17]([O-])=O.[Na+].[CH3:21][C:22](=[O:27])[CH2:23][C:24](=[O:26])[CH3:25].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[N:5]1[CH:6]=[CH:7][C:2]([NH:1][N:17]=[C:23]([C:22](=[O:27])[CH3:21])[C:24](=[O:26])[CH3:25])=[CH:3][CH:4]=1

Participants

9

Reactant 7

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 17274-AminopyridineHCID 10340Sodium CarbonateHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468361HCID 178468361, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-6 °C

Procedure

4-Aminopyridine (470 mg, 5.00 mmol) was added to a solution of 3 mL of phosphoric acid (85%) and 2 mL of nitric acid (65%) at −6° C. When the mixture reached to room temperature it was cooled to −6° C. and solid sodium nitrite (350 mg, 5.00 mmol) was added during 10 min. Small pieces of ice (50 g) were added into the solution. The mixture was added at 0° C. to a suspension of corresponding 2,4-pentanedione (500 mg, 5.00 mmol) and potassium acetate (20 g) in ethanol (250 mL). The solution was stirred for 15 min, added to 250 mL of saturated Na2CO3 aqueous solution, extracted with dichloromethane, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give 3-(pyridin-4-ylhydrazono)pentane-2,4-dione (149 mg, yield 14%).

Workup

  1. customreached to room temperature
  2. extractionextracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eaa698c34d4647fc9ceae2977cd2758c
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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