Dimethylamine → 6-((Dimethylamino)methyl)-3-pyridinecarboxylic acid

HRID 906915Notes

Reaction equation

HRID 906915 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1.[CH3:12][NH:13][CH3:14]>CCO>[NH3:4].[CH3:12][N:13]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)[CH3:14]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 218409786-(Bromomethyl)-3-pyridinecarboxylic acid

Product 2

HCID 222AmmoniaYield 1%HCID 575737456-((Dimethylamino)methyl)-3-pyridinecarboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2nd step: To a stirred solution of 6-bromomethyl-nicotinic acid (350 mg, 1.62 mmol) in EtOH (3 mL) was added a solution of dimethyl-amine in EtOH (2 mL, 30% solution). Stirring was continued for 1 hour, concentrated under vacuo. Column chromatography (SiO2, CH2Cl2/MeOH: 8/2, aq. NH3 1%) yielded 205 mg (70%) of 6-dimethylaminomethyl-nicotinic acid as a light brown solid. ES-MS m/e: 181.1 (M+H+).

Workup

  1. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-e3254bb8d29d4baaaaec976878d6975a
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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