3-Aminopicolinic acid → Methyl 3-aminopyridine-2-carboxylate
Reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][Si](C=[N+]=[N-])(C)C>CO.C(OCC)C.C(OCC)(=O)C>[CH3:11][O:9][C:8]([C:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
400 mg (2.9 mmol) of 3-amino-pyridine-2-carboxylic acid was dissolved in 3 mL of methanol. To this solution 1.6 mL of 2 M (trimethylsilyl)diazomethane solution in diethyl ether was added dropwise at 0° C., followed by stirring of the mixture for 2 hours at room temperature The solution was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution. Flash chromatography afforded the ester product. LC-MSD, m/z for C7H8N2O2[M+H]+=153.0; HPLC retention time: 0.2 minutes.
Workup
- washwashed with aqueous sodium bicarbonate solution
Sources & evidence
- ORD record
- ord-d01cf5b94815459f9d5a0733a731beb8
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394307B2
Reaction notes
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