Methyl iodide → Methyl 2-aminopyridine-3-carboxylate

HRID 1647717Notes

Reaction equation

HRID 1647717 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:11])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 729302-Aminonicotinic acid

Product 1

HCID 351633Methyl 2-aminopyridine-3-carboxylateYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

The 2-aminonicotinic acid (5.0 g, 0.0362 mol) and K2CO3 (5.0 g, 0.0362 mol) were suspended in 50 ml of DMF and heated to reflux. Almost complete solution occurred. The mixture was cooled to 25° C. and the CH3I (5.1 g/2.2 ml, 0.0362 mol) was added and the mixture was stirred 18 hours. The mixture was filtered and concentrated. The residue was placed on a bed of silica and eluted with 5%/EtOH/CH2Cl2 /1/10% NH4OH. The fractions containing the product were combined and concentrated. The residue was suspended in Et2O, filtered and washed with Et2O to yield 3.2 g (58%) the title compound.

Workup

  1. temperatureheated to reflux
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. washeluted with 5%/EtOH/CH2Cl2 /1/10% NH4OH
  5. additionThe fractions containing the product
  6. concentrationconcentrated
  7. filtrationfiltered
  8. washwashed with Et2O

Sources & evidence

ORD record
ord-fcf2658390b143fcb926d67e8e5cd4cc
Source dataset
uspto-grants-1995_07
Patent number
US05434161

Reaction notes

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