Pyridine → HCID 870147, compound

HRID 2110997Notes

Reaction equation

HRID 2110997 reaction equation
ClN1C(=O)CCC1=O.N1C=CC=CC=1.[CH3:15][C:16]1[CH:24]=[CH:23][C:19]([CH:20]=[N:21][OH:22])=[CH:18][CH:17]=1.[N+](C1C=C[C:31]([C:32]([O:34][CH:35]=CC(OC)=O)=[O:33])=[CH:30]C=1)([O-])=O.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:16]1([CH3:15])[CH:24]=[CH:23][C:19]([C:20]2[C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][O:22][N:21]=2)=[CH:18][CH:17]=1

Participants

8

Reactant 6

HCID 1049PyridineHCID 8471TriethylamineHCID 19475HCID 19475, compoundHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 2763952HCID 2763952, compound

Product 1

HCID 870147HCID 870147, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-Chlorosuccinimide (9.87 g, 73.4 mmol) and pyridine (175 mg, 2.2 mmol) were dissolved in chloroform (100 ml), 4-methylbenzaldehyde oxime (10 g, 73.4 mmol) was added, and the mixture was stirred until it became clear. A solution of 2-methoxycarbonylvinyl 4-nitrobenzoate (9.22 g, 36.7 mmol) and triethylamine (12.9 g, 128 mmol) in chloroform (180 ml) was slowly added dropwise at 0° C. over 2 hours, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=5:95) to give the title compound (1.56 g, 7.19 mmol, 19.6%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (hexane:ethyl acetate=5:95)

Sources & evidence

ORD record
ord-d9b52a51d7ac442c9794c2fb601396e9
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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