Triethylamine → Methyl 2-aminopyridine-3-carboxylate

To a mixture of 2-aminonicotinic acid (n) (30.0 g 217 mmol) and 2-chloro1,3-dimethyl imidazolinium chloride (55.2 g 326 mmol) in MeOH (750 ml) was added dropwise triethylamine (91 ml 652 mmol). The resultant mixture was stirred at room temperature for 1 h. The mixture was then evaporated under reduced pressure to afford a residue. The residue was purified by extraction with ethyl acetate (300 ml×2). The combined organic phase was washed with water (200 ml×2) and brine (200 ml). Dried over anhydrous sodium sulfate, filtered and concentrated to give an essentially pure methyl 2-aminonicotinate (31.3 g, yield 94%). This compound was used in next step without further purification.

1. customThe mixture was then evaporated under reduced pressure
2. customto afford a residue
3. customThe residue was purified by extraction with ethyl acetate (300 ml×2)
4. washThe combined organic phase was washed with water (200 ml×2) and brine (200 ml)
5. dry with materialDried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-882e3f1cc7fd429289a5ebc08e82eb17

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151182B2