3-Aminopicolinic acid → Methyl 3-aminopicolinate

HRID 1363047Notes

Reaction equation

HRID 1363047 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

HCID 738363-Aminopicolinic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 9898880Methyl 3-aminopicolinate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

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

  1. washwashed with aqueous sodium bicarbonate solution

Sources & evidence

ORD record
ord-73302f59b2374be49c7d6cffe077259c
Source dataset
uspto-grants-2011_02
Patent number
US07884110B2

Reaction notes

Loading…