Pyridine → 4-Iodo-N-methoxy-N-methyl-benzamide

HRID 489476Notes

Reaction equation

HRID 489476 reaction equation
N1C=CC=CC=1.[I:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1.Cl.[CH3:18][NH:19][O:20][CH3:21]>ClCCl>[CH3:21][O:20][N:19]([CH3:18])[C:12]([C:11]1[CH:15]=[CH:16][C:8]([I:7])=[CH:9][CH:10]=1)=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 743734-Iodobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 54617564-Iodo-N-methoxy-N-methyl-benzamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyridine (104 g, 1.32 mol) in dichloromethane (150 ml) was added dropwise to a suspension of 4-iodobenzoyl chloride (251 g, 0.94 mol) and N,O-dimethylhydroxylamine hydrochloride (97 g, 0.94 mol) in dichloromethane (850 ml) at 0° C. The mixture was allowed to warm to room temperature and was stirred for 18 hours. The solution was evaporated under reduced pressure, the residue was dissolved in ethyl acetate (1 l), and was then washed with dilute hydrochloric acid (2N, 3×400 ml) and saturated sodium bicarbonate solution (300 ml) and dried (Na2SO4). The organic extract was evaporated under reduced pressure. The residue was purified by distillation to yield the subtitle compound (241 g, 93%) as a yellow oil, b.p. 130° C. (0.1 mm Hg), which was characterized by 1H NMR.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (1 l)
  3. washwas then washed with dilute hydrochloric acid (2N, 3×400 ml) and saturated sodium bicarbonate solution (300 ml)
  4. dry with materialdried (Na2SO4)
  5. extractionThe organic extract
  6. customwas evaporated under reduced pressure
  7. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-eec875b2509149c8aa328e30453f2701
Source dataset
uspto-grants-2005_12
Patent number
US06977302B2

Reaction notes

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