Isonicotinamide → HCID 178484338, compound

HRID 1931546Notes

Reaction equation

HRID 1931546 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(O[CH:13](OCC)[N:14]([CH3:16])[CH3:15])C>>[CH3:13][N:14](/[CH:16]=[N:9]/[C:1]([C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[O:8])[CH3:15]

Participants

3

Reactant 2

HCID 15074IsonicotinamideHCID 70913Dimethylformamide diethylacetal2×

Product 1

HCID 178484338HCID 178484338, compoundYield 100.6%

Conditions

Temperature
120 °C

Procedure

Isonicotinamide (2.00 g, 16.38 mmol) and N,N-dimethylformamide diethyl acetal (2.8 ml, 16.38 mmol) were combined and heated to 120° C. A short path distillation apparatus was used to collect the ethanol that was liberated during the reaction. The reaction mixture was an orange solution. After 15 minutes, additional N,N-dimethylformamide diethyl acetal (1.0 ml, 5.83 mmol) was added to the reaction mixture. After 1.5 hours, the reaction mixture was cooled to room temperature. The reaction mixture solidified upon cooling and was placed under high vacuum overnight to give the title compound (2.92 g, 16.48 mmol) as a yellow solid.

Workup

  1. distillationA short path distillation apparatus
  2. customto collect the ethanol that
  3. customwas liberated during the reaction
  4. waitAfter 1.5 hours
  5. temperaturethe reaction mixture was cooled to room temperature
  6. temperatureupon cooling
  7. customwas placed under high vacuum overnight

Sources & evidence

ORD record
ord-ba6b3109fe8a447da679cc4e31f7c148
Source dataset
uspto-grants-2012_05
Patent number
US08188085B2

Reaction notes

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