Picolinic acid → N-Methoxy-N-methylpicolinamide

HRID 735458Notes

Reaction equation

HRID 735458 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:23][NH:24][O:25][CH3:26].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:26][O:25][N:24]([CH3:23])[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 11829796N-Methoxy-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Picolinic acid (12.3 g, 100 mmol), N,N-carbonyldiimidazole (17.8 g, 110 mmol) and anhydrous CH2Cl2 (150 mL) were combined and stirred at room temperature for 60 minutes. To the reaction mixture was added a solution of N,O-dimethylhydroxylamine hydrochloride (10.7 gr, 0.11 mole), anhydrous CH2Cl2 (50 mL) and diisopropylethylamine (20 mL), and stirring continued overnight. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel 60, MeOH/CH2Cl2, 9:1) to afford pyridine-2-carboxylic acid methoxy-methyl-amide (a pale yellow liquid, 15.9 g, 95%); ESI) m/z 167.

Workup

  1. stirringstirring continued overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash chromatography (silica gel 60, MeOH/CH2Cl2, 9:1)

Sources & evidence

ORD record
ord-8d548103e341436fb98bfc99a4287d7c
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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