6-Aminonicotinic acid → 6-Aminonicotinamide

HRID 2295023Notes

Reaction equation

HRID 2295023 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.O[N:12]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH2:12])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 184966-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 95006-AminonicotinamideYield 162.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-aminopyridine-3-carboxylic acid (8.36 g), N-hydroxybenzotriazole (10.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (12.8 g) and 4-dimethylaminopyridine (8.12 g) in N,N-dimethylformamide (300 ml) was stirred at 0° C. for 15 minutes. (2E,4E)- and (2Z,4E)-4-methyl-2,4-heptadien-1-ylamine (7.7 g) was added to the mixture. The solution was stirred at 0° C. for 2 hours and then at room temperature overnight. The mixture was evaporated in vacuo and the residue was diluted with water. The resulting precipitate was filtered and washed with water to give N-[(2E,4E)- and (2Z-4E)-4-methyl-2,4-heptadien-1-yl]-6-amino-3-pyridinecarboxamide (13.5 g).

Workup

  1. stirringThe solution was stirred at 0° C. for 2 hours
  2. customat room temperature
  3. customovernight
  4. customThe mixture was evaporated in vacuo
  5. additionthe residue was diluted with water
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-e30d40e286394fe298abf46b82754f5a
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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