Acetic Acid → Nicotinic Acid

HRID 900725Notes

Reaction equation

HRID 900725 reaction equation
C(NN)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C[Si](N=C=S)(C)C.[C:18]([OH:21])(=[O:20])C>>[C:18]([OH:21])(=[O:20])[C:3]1[CH:2]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 3767IsoniazidHCID 75297Isothiocyanatotrimethylsilane

Product 1

HCID 938Nicotinic Acid

Conditions

Temperature
105 °C

Procedure

Isonicotinic acid hydrazide (1.06 g, 7.73 mmol) and trimethylsilyl isothiocyanate (2.03 g, 15.4 mmol) were dissolved in acetic acid (2.0 ml) in a round bottom flask with a condenser and stirred magnetically at 105° C. overnight. The solution was cooled to room temperature, at which time a solid formed. The acetic acid solution was decanted and any remaining solvent was evaporated with heating on a rotary evaporator. This residue was carried on as such to the next step.

Workup

  1. temperatureThe solution was cooled to room temperature, at which time a solid
  2. customformed
  3. customThe acetic acid solution was decanted
  4. customany remaining solvent was evaporated
  5. temperaturewith heating on a rotary evaporator

Sources & evidence

ORD record
ord-05a68a2e57f940b1a05cc3d4a0efe12f
Source dataset
uspto-grants-2008_04
Patent number
US07361669B2

Reaction notes

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