Triethylamine → N,2-Dimethoxy-N-methylnicotinamide

HRID 1898149Notes

Reaction equation

HRID 1898149 reaction equation
[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH3:12][NH:13][O:14][CH3:15].CCN(CC)CC.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([N:13]([O:14][CH3:15])[CH3:12])=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 111923Propylphosphonic anhydrideHCID 7080932-Methoxynicotinic acid

Product 1

HCID 45871212N,2-Dimethoxy-N-methylnicotinamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled mixture of 2-methoxy-nicotinic acid (2 g, 13.05 mmol), N,O-dimethylhydroxylamine (1.91 g, 19.59 mmol) in CH2Cl2 (20 mL) and Et3N (7.26 mL, 15.66 mmol) was added 1-propane phosphonic acid cyclic anhydride (9.96 mL, 15.66 mmol; 50 wt % solution in EtOAc) dropwise and stirred at room temperature for 2 h. The reaction mixture was filtered, washed with CH2Cl2 (10 mL), evaporated to dryness and subjected to column chromatography (SiO2, 50% EtOAc-hexanes) to obtain 2,N-dimethoxy-N-methyl-nicotinamide (2.33 g) in 91% yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with CH2Cl2 (10 mL)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-32a34593a43f4cd6bad223850bb951cf
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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