Triethylamine → 6-(Methoxy-methyl-carbamoyl)-nicotinic acid methyl ester

HRID 2242217Notes

Reaction equation

HRID 2242217 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:27][NH:28][O:29][CH3:30].C(N(CC)CC)C>ClCCl.CN(C=O)C.ClCCCl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:13])[N:28]([O:29][CH3:30])[CH3:27])=[N:9][CH:10]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acid

Product 1

HCID 108895416-(Methoxy-methyl-carbamoyl)-nicotinic acid methyl esterYield 81%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of pyridine-2,5-dicarboxylic acid-5-methyl ester (1.0 g, 5.52 mmol), 1,1′-carbonyldiimidazole (0.984 g, 6.07 mmol), 1,2-dichloroethane (30.0 mL) and DMF (8.0 mL) was stirred at room temperature for 1 hour. To the reaction mixture was added N,O-dimethylhydroxylamine hydrochloride (0.535 g, 5.52 mmol) and triethylamine (1.15 mL, 8.28 mmol) and stirred at room temperature for 12 hours. The reaction was diluted with dichloromethane (20.0 mL) and washed with water, 0.5N HCl and saturated NaHCO3, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (1.0 g, 81% yield).

Workup

  1. washwashed with water, 0.5N HCl and saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c18e2b382f13459d9ab964764eb79629
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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