Isonicotinic Acid → 4-Isocyanatopyridine

HRID 2102732Notes

Reaction equation

HRID 2102732 reaction equation
C(O)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.C([N:29]([CH2:32]C)CC)C>C1(C)C=CC=CC=1>[N:29]([C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1)=[C:32]=[O:17]

Participants

5

Reactant 3

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 116367964-Isocyanatopyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of isonicotinic acid (0.369 g, 3 mmol) (Aldrich) in toluene (15 mL) was added diphenylphosphoryl azide (0.958 g, 3.5 mmol) (Aldrich), followed by the addition of triethylamine (0.35 g, 3.6 mmol) (Aldrich). The mixture was stirred at room temperature for 30 minutes and the mixture became clear. Then the mixture was heated at 80° C. for 2 hours. The mixture was cooling down to room temperature to give crude 4-isocyanato-pyridine as 0.2 M solution of toluene and used for the next step without further purification.

Workup

  1. temperatureThen the mixture was heated at 80° C. for 2 hours
  2. temperatureThe mixture was cooling down to room temperature

Sources & evidence

ORD record
ord-4c052b5908ee4cbd9823b25840b7ebd4
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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