Pyridine → 4-Iodo-N-methoxy-N-methyl-benzamide
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 (IL), 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 title product (241 g, 93%), as a yellow oil b.p. 130° C. (0. Imm Hg), which was characterised by 1H-N.M.R. spectroscopy (300 MHz, CDCl3): δ=3.32 (s,3H), 3.50 (s,3H), 7.40 (d,2H), 7.72 (d,2H) ppm.
Workup
- customThe solution was evaporated under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate (IL)
- washwas then washed with dilute hydrochloric acid (2N, 3×400 ml) and saturated sodium bicarbonate solution (300 ml)
- dry with materialdried (Na2SO4)
- extractionThe organic extract
- customwas evaporated under reduced pressure
- distillationThe residue was purified by distillation
Sources & evidence
- ORD record
- ord-d92da1acf08440a8b54f70b5906dd712
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06015825
Reaction notes
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