Triethylamine → 2,6-Dichloro-N-methoxy-N-methylisonicotinamide

HRID 2214485Notes

Reaction equation

HRID 2214485 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[CH3:18][NH:19][O:20][CH3:21].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([N:19]([O:20][CH3:21])[CH3:18])=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 65578Oxalyl chlorideHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 219482182,6-Dichloro-N-methoxy-N-methylisonicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2,6-dichloroisonicotinic acid (20.0 g, 0.10 mol) and oxalylchloride (11.2 ml, 0.13 mol) in methylenechloride (100 ml) is stirred at room temperature in the presence of a katalytic amount of dimethylformamide for 2 hours to give a clear solution. The solvent is evaporated under reduced pressure and the residue is added to a well stirred solution of N,O-dimethylhydroxylamine (12.0 g, 0.2 mol) and triethylamine (10.2 g, 0.1 mol) at 0–5° C. After stirring for 2 hours at room temperature the reaction mixture is washed with water. The organic phase is dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 2,6-dichloro-N-methoxy-N-methyl-isonicotinamide in form of colorless crystals, m.p. 69–70° C.

Workup

  1. customto give a clear solution
  2. customThe solvent is evaporated under reduced pressure
  3. additionthe residue is added to a well
  4. washis washed with water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a39cd8e1f3d142c8887b80d161840719
Source dataset
uspto-grants-2006_09
Patent number
US07109197B2

Reaction notes

Loading…