Pyridine → 4-Chloro-N-methoxy-N-methylbenzamide

HRID 623947

Reaction equation

HRID 623947 reaction equation
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([N:9]([O:10][CH3:11])[CH3:8])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 112756634-Chloro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (27.6 mL, 343 mmol) was added to N,O-dimethylhydroxylamine hydrochloride (16.7 g, 172 mmol) in DCM (400 mL). 4-Chlorobenzoyl chloride (20 mL, 156 mmol) was then added and the mixture was stirred at room temperature for 3 days. Solids were removed by vacuum filtration, washing with DCM. The filtrate was washed with 1 N aqueous HCl followed by water. The organic phase was dried (Na2SO4), filtered, and concentrated, affording the crude title compound as a colorless liquid which was used without purification in the next step.

Workup

  1. customSolids were removed by vacuum filtration
  2. washwashing with DCM
  3. washThe filtrate was washed with 1 N aqueous HCl
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0b43466913e84e2bae57fdc66e5da223
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Linked notes

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