Dimethylformamide → HCID 178521113, compound

HRID 1526117Notes

Reaction equation

HRID 1526117 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[OH:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14]>ClCCl.ClCCCl>[OH:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([Cl:3])=[O:14]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178418543HCID 178418543, compound

Product 1

HCID 178521113HCID 178521113, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

20 ml (270 mmol) of thionyl chloride and 1 ml of dimethylformamide are added respectively to 12.5 g (90 mmol) of 2-hydroxynicotinic acid in suspension in a mixture of 80 ml of dichloromethane and 20 ml of 1,2-dichloroethane. The suspension is stirred at reflux for 2.5 hours. The reaction mixture is cooled to room temperature and the precipitate formed is filtered to yield (11.98 g) of 2-hydroxynicotinic chloride. The solid is suspended in 150 ml of dichloromethane, and then 7.42 g (76 mmol) of N,O-dimethylhydroxylamine hydrochloride and 21.37 ml (152 mmol) of triethylamine are added successively. The reaction mixture is stirred for 2 hours at room temperature, the solvent is evaporated, and then the solid is taken up in a minimum of ethyl acetate (70 ml). The solid is filtered (triethylamine salt) and the filtrate is concentrated to yield after purification by silica gel chromatography (eluent: 10:1 dichloromethane/methanol) 10.5 g (64%) of N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide in the form of a white solid.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customthe precipitate formed
  3. filtrationis filtered

Sources & evidence

ORD record
ord-155f98b7e74f49019f16c142382a91ff
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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