Formic Acid → 6-Formamidopyridine-3-carboxamide

HRID 1391303Notes

Reaction equation

HRID 1391303 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[OH-].[Na+].[CH:13](O)=[O:14]>>[CH:13]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1)=[O:14]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 95006-AminonicotinamideHCID 14798Sodium Hydroxide

Product 1

HCID 213308846-Formamidopyridine-3-carboxamide

Conditions

Temperature
100 °C

Procedure

6-Aminonicotinamide, 5.6 g, was added to 90% formic acid, 15 ml. After all the crystals were dissolved, the clear solution was heated to 100° C. for 10 minutes. The mixture was cooled and then 4N NaOH was added to adjust the pH to 2.8. The white crystals which formed were separated by filtration and were washed once with cold water followed by acetone wash. The yield of 6-formylaminonicotinamide was 5.6 g. This product had Rf value of 0.53 on thin-layer chromatogram using a solvent system of benzene:methanol, 1:1.

Workup

  1. dissolutionAfter all the crystals were dissolved
  2. temperatureThe mixture was cooled
  3. customThe white crystals which formed
  4. customwere separated by filtration
  5. washwere washed once with cold water
  6. washwash

Sources & evidence

ORD record
ord-cecccd88c55f498e9ef578e8041dad2d
Source dataset
uspto-grants-1979_02
Patent number
US04141977

Reaction notes

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