Isonicotinic Acid → HCID 11701058, compound

HRID 1736390Notes

Reaction equation

HRID 1736390 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>CC(C)=O.O>[N:5]1[CH:6]=[CH:7][C:2]([C:1]([N:23]=[N+:24]=[N-:25])=[O:9])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium Azide

Product 1

HCID 11701058HCID 11701058, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

6.15 g of isonicotinic acid and 5.55 g of triethylamine were dissolved in 50 ml of acetone. 6 g of ethyl chloroformate were added dropwise to this solution which had been cooled to -10° C. After 2 hours a solution of 5 g of NaN3 dissolved in 20 ml of H2O was added dropwise at 0° C. After 1 hour at room temperature the solid was filtered off and discarded. The solution was distilled at room temperature and the residue was extracted with dichloromethane. After drying over MgSO4 the solvent was distilled off and the liquid remaining behind was filtered over silica gel with dichloromethane as the eluent. There was obtained 4-pyridylcarboxylic acid azide as a colorless liquid which crystallized in a deep freezer (-18° C.). IR: 2141, 2190 cm-1 (N3).

Workup

  1. additionwas added dropwise at 0° C
  2. filtrationAfter 1 hour at room temperature the solid was filtered off
  3. distillationThe solution was distilled at room temperature
  4. extractionthe residue was extracted with dichloromethane
  5. dry with materialAfter drying over MgSO4 the solvent
  6. distillationwas distilled off
  7. filtrationthe liquid remaining behind was filtered over silica gel with dichloromethane as the eluent

Sources & evidence

ORD record
ord-1b9b5e8acbc840dea71bdafa8159bf1c
Source dataset
uspto-grants-1996_07
Patent number
US05541186

Reaction notes

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