Potassium Carbonate → 2-(methylamino)pyridine-3-carboxylic acid

HRID 2194510Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:12][NH2:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]Br>[CH3:12][NH:13][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

30.0 g (0.19 mol) of 2-chloronicotinic acid was dissolved in N,N-dimethylformamide (400 mL), and 31.0 g (0.38 mol) of methylamine hydrochloride, 105 g (0.76 mol) of potassium carbonate, and 2.73 g (19.0 mmol) of copper(I) bromide were added to the solution. The mixture was stirred for 20 hours at 100° C. After the mixture was cooled to room temperature, insoluble materials were filtered off, and the filtrate was concentrated. A 10% aqueous solution of sodium hydroxide was added to the residue thus obtained, and the mixture was washed with diethyl ether. Concentrated hydrochloric acid was added to the aqueous phase to adjust the aqueous phase to pH 6 to 7, and a solid obtained by concentrating the aqueous phase was dried. Thus, crude 2-(methylamino)nicotinic acid was obtained.

Workup

temperatureAfter the mixture was cooled to room temperature
filtrationinsoluble materials were filtered off
concentrationthe filtrate was concentrated
additionA 10% aqueous solution of sodium hydroxide was added to the residue
customthus obtained
washthe mixture was washed with diethyl ether
additionConcentrated hydrochloric acid was added to the aqueous phase
customa solid obtained
concentrationby concentrating the aqueous phase
customwas dried

Sources & evidence

ORD record: ord-5714487ead934a9597eadc4be20e92de
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334236B2

Reaction notes

Loading…