Pyridine → N-Methoxy-N,4-dimethylbenzamide

HRID 1271262

Reaction equation

HRID 1271262 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].N1C=CC=CC=1>ClCCl>[CH3:15][O:14][N:13]([CH3:12])[C:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 134054-Methylbenzoyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 5133773N-Methoxy-N,4-dimethylbenzamideYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.00 g of p-toluoyl chloride in 300 ml of dichloromethane, 6.94 g of N,O-dimethylhydroxyamine hydrochloride was added. The reaction solution was ice-cooled and 11.5 ml of pyridine was added dropwise. After the completion of dropwise addition, the mixture was stirred at room temperature for one hour and the solvent was evaporated under reduced pressure. The residue was combined with water, extracted with diethyl ether and then washed in turn with 10% hydrochloric acid, water and an aqueous saturated sodium hydrogen carbonate solution. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain 10.40 g of the desired compound as a colorless oily substance.

Workup

  1. temperaturecooled
  2. additionAfter the completion of dropwise addition
  3. customthe solvent was evaporated under reduced pressure
  4. extractionextracted with diethyl ether
  5. washwashed in turn with 10% hydrochloric acid, water
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-04e4233c137646ee8cd244384cd648f1
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Linked notes

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