Picolinic acid → N-Methoxy-N-methylpicolinamide

HRID 473620Notes

Reaction equation

HRID 473620 reaction equation
CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([OH:30])=O.Cl.[CH3:32][NH:33][O:34][CH3:35]>CN(C)C=O.C(N(CC)CC)C>[CH3:35][O:34][N:33]([CH3:32])[C:28](=[O:30])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 11829796N-Methoxy-N-methylpicolinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

EDCI (2.30 g, 0.012 mol) and 1-hydroxy benztriazole (1.36 g, 0.009 mol) were added o a stirred solution of pyridine-2-carboxylic acid (1.0 g, 0.008 mol) in N,N-dimethyl formamide (16 mL) at 0° C. The reaction mixture was allowed to stir for 15 min then triethyl amine was added followed by addition of N,O-dimethyl hydroxyl amine hydrochloride at 0° C. The resulting mixture was stirred at RT overnight. The reaction mixture was partitioned between water (30 mL) and ethyl acetate (2×30 mL). The organic layer was dried over sodium sulphate and concentrated. The crude product was purified by column chromatography using 100-200 mesh silica gel and 0-20% EtOAc: Hexane as eluant to obtain product.

Workup

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customThe reaction mixture was partitioned between water (30 mL) and ethyl acetate (2×30 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. customHexane as eluant to obtain product

Sources & evidence

ORD record
ord-55e299da700b414f951fee12561adbde
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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