4-Aminopyridine → HCID 87536091, compound

HRID 714552Notes

Reaction equation

HRID 714552 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[N:8]([O-])=O.[Na+].[CH3:12][C:13]([CH2:15][C:16]([CH3:18])=[O:17])=[O:14].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>P(=O)(O)(O)O.[N+]([O-])(O)=O.CCO>[N:1]1[CH:6]=[CH:5][C:4]([N:7]=[N:8][CH:15]([C:16](=[O:17])[CH3:18])[C:13](=[O:14])[CH3:12])=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 17274-AminopyridineHCID 10340Sodium CarbonateHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 87536091HCID 87536091, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 944Nitric AcidSolventHCID 1004Phosphoric AcidSolvent

Procedure

A solution of pyridine-4-ylamine (4.5 g, 47.81 mmol) in 85% phosphoric acid (30 ml) and 65% nitric acid (20 ml) was cooled to −10° C. and treated with solid sodium nitrite (3.3 g, 47.8 mmol) over 20 mins. Ice (50 g) was added and the mixture added at 0° C. to a suspension of 2,4-pentadione (4.79 g; 47.8 mmol) and potassium acetate (40 g) in EtOH (280 ml). After completion, 20% aq. Na2CO3 (300 ml) was added at 0° C. until pH reached 7 and the solution extracted with dichloromethane (3×400 ml), dried, concentrated and chromatographed on silica gel with dichloromethane/methanol to give the product as a yellow solid (5.3 g, 54%).

Workup

  1. extractionthe solution extracted with dichloromethane (3×400 ml)
  2. customdried
  3. concentrationconcentrated
  4. customchromatographed on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-9d99a57558754314a0c3115851c6ef1d
Source dataset
uspto-grants-2015_11
Patent number
US09187455B2

Reaction notes

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