Hydrochloric Acid → 2-Chloro-6-(methylamino)pyridine-4-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](Cl)[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:12][NH2:13].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH:13][CH3:12])[N:10]=1)[C:5]([OH:7])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2,6-dichloroisonicotinic acid (25 g, 130.2 mmol) in 52 mL water was added 60 mL of 40% methylamine in water. Reaction heated to reflux at 100° C. After 16 h, reaction was cooled to rt. Reaction was acidified with 1N HCl (200 mL) and extracted with EtOAc (300 mL×4). The combined organics were washed with brine (150 mL), dried over Mg2SO4, filtered, and concentrated in vacuo to give 24.2 g (100%) of 2-chloro-6-(methylamino)isonicotinic acid as a brown solid. LC/MS [M+H]+ 187.0.
Workup
- customReaction
- temperatureheated
- customreaction
- temperaturewas cooled to rt
- customReaction
- extractionextracted with EtOAc (300 mL×4)
- washThe combined organics were washed with brine (150 mL)
- dry with materialdried over Mg2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6901ad96f0314c1fbec018c3f8b9170d
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394837B2
Reaction notes
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