Diethyl Ether → 2-Chloro-N-methoxy-N-methylisonicotinamide

HRID 1635512Notes

Reaction equation

HRID 1635512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](O)=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:24][NH:25][O:26][CH3:27].CCOCC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[N:25]([CH3:24])[O:26][CH3:27])[CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2369852-Chloroisonicotinic acid

Product 1

HCID 185068942-Chloro-N-methoxy-N-methylisonicotinamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-chloroisonicotinic acid (18.0 g, 0.105 mol) in 250 mL of methylenechloride was added 1,1′-carbonyldiimidazole (17.0 g, 0.105 mol) portionwise. The mixture was stirred for 0.5 h and N,O-dimethylhydroxylamine hydrochloride (10.2 g, 0.105 mol) was added rapidly. The reaction mixture was stirred at room temperature overnight. Ether was added and the organic layer was washed with water, dried, dried over magnesium sulfate and filtered. The filtrate was concentrated to give 14.5 g (70%) of product as a yellow oil. This was used in next step without purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washthe organic layer was washed with water
  3. customdried
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-de5715e0d7f44fc8b5f2ca8e4f42bada
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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