Carbamate → 2-Amino-N-methylpyridine-3-carboxamide

HRID 215685Notes

Reaction equation

HRID 215685 reaction equation
[NH:1]1[C:6]2C=N[O:9][CH2:10][C:5]=2[C:4](=O)[CH2:3][C:2]1=O.C[NH2:14].[C:15](=O)([O-])[NH2:16].C(=O)=O>O1CCOCC1.C(O)C>[CH3:15][NH:16][C:10](=[O:9])[C:5]1[CH:4]=[CH:3][CH:2]=[N:1][C:6]=1[NH2:14]

Participants

7

Reactant 4

HCID 276CarbamateHCID 280Carbon DioxideHCID 6329MethylamineHCID 67131340HCID 67131340, compound

Product 1

HCID 205853262-Amino-N-methylpyridine-3-carboxamideYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

14.96 g (0.09 mol) of 1H-Pyrido[2,3-d]oxazin-2,4-dione was suspended in 138 ml dioxane. The mixture is heated to 40° C. and 17 ml of a 33% solution of methyl amine in ethanol is added dropwise directly into the reaction mixture, to avoid carbamate formation with the evolving CO2. The reaction is allowed to continue for 90 minutes. After cooling down to room temperature, the formed precipitate is removed by filtration and the filtrate is concentrated to dryness. 13.2 g (97%) of 2-aminonicotinic acid methyl amide was isolated (m.p. 140-2° C.).

Workup

  1. temperatureAfter cooling down to room temperature
  2. customthe formed precipitate is removed by filtration
  3. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-b2fff7c590ea4b8b851c57434f503c61
Source dataset
uspto-grants-2012_06
Patent number
US08192918B2

Reaction notes

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