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

HRID 2194510
Notes
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Reaction equation

HRID 2194510 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 47385172-(Methylamino)pyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 6228
Dimethylformamide
Solvent

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

  1. temperatureAfter the mixture was cooled to room temperature
  2. filtrationinsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated
  4. additionA 10% aqueous solution of sodium hydroxide was added to the residue
  5. customthus obtained
  6. washthe mixture was washed with diethyl ether
  7. additionConcentrated hydrochloric acid was added to the aqueous phase
  8. customa solid obtained
  9. concentrationby concentrating the aqueous phase
  10. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes