1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-hydroxy-N-methoxy-N-methylpicolinamide

HRID 573320Notes

Reaction equation

HRID 573320 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 866889815-hydroxy-N-methoxy-N-methylpicolinamideYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-hydroxypicolinic acid (5.00 g), N,O-dimethylhydroxylamine hydrochloride (3.86 g), TEA (11.1 mL), WSC (7.58 g) and HOBt (5.34 g) in DMF (100 mL) was stirred at room temperature for 24 h. The mixture was poured into 5% NaHCO3 aqueous solution and extracted with AcOEt (10 times). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (4.13 g).

Workup

  1. extractionextracted with AcOEt (10 times)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-39efe113bc814bf8a0724b768be5c74b
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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