Hydrochloric Acid → 2-Chloro-N-methoxy-N-methylnicotinamide

HRID 1898144Notes

Reaction equation

HRID 1898144 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(=O)(O)[O-].[Na+].Cl.[CH3:17][NH:18][O:19][CH3:20].Cl>C1COCC1.O>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:18]([O:19][CH3:20])[CH3:17])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 102360762-Chloro-N-methoxy-N-methylnicotinamideYield 87.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 2-chloro-nicotinoyl chloride (7.00 g, 39.8 mmol) and sodium bicarbonate (10.0 g, 119 mmol) in 1:1 THF/H2O (110 mL) at 0° C. was added N,O-dimethyl hydroxylamine hydrochloride (4.68 g, 47.7 mmol). The resultant solution was stirred 2 h at 0° C., neutralized with 10% HCl to pH ˜7, and the aqueous layer was extracted two times with EtOAc. The combined organics were dried with sodium sulfate and concentrated in vacuo to produce 6.96 g (87%) of the crude nicotinamide, which was used without further purification.

Workup

  1. extractionthe aqueous layer was extracted two times with EtOAc
  2. dry with materialThe combined organics were dried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04b2dde1b3854376975e628f47cfec86
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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