Pyridine → HCID 20249393, compound

HRID 1285552Notes

Reaction equation

HRID 1285552 reaction equation
C1C=C[NH+]=CC=1.Br[Br-]Br.[CH2:10]([C:12]1[NH:13][C:14]([CH2:33][CH3:34])=[C:15]([C:29]([O:31][CH3:32])=[O:30])[CH:16]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:17]=1[C:18]([O:20]C)=[O:19])[CH3:11].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:33]([C:14]1[NH:13][C:12]2[CH:10]([CH3:11])[O:20][C:18](=[O:19])[C:17]=2[CH:16]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[C:15]=1[C:29]([O:31][CH3:32])=[O:30])[CH3:34]

Participants

4

Reactant 2

HCID 1049PyridineHCID 20249385HCID 20249385, compound

Product 1

HCID 20249393HCID 20249393, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In a similar manner 2.02 grams (2.52 grams of 80 percent; 6.31 millimoles) of pyridinium bromide perbromide is added in a single portion to a cooled to 0° C. solution of 1.91 grams (5.26 millimoles) of dimethyl 2,6-diethyl-4-(4-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.79 gram (10.1 millimoles) of pyridine in 40 milliliters of chloroform. The resulting mixture is stirred at this temperature for 30 minutes, then at reflux temperature for 90 minutes. The mixture is then allowed to cool, diluted with chloroform, the diluted solution washed with 2N hydrochloric acid and brine, and dried; the solvent then is evaporated to obtain the methyl 2-ethyl-4-(4-chlorphenyl)-5-oxo-7-methyl-1,4,5,7-tetrahydrofuro[3,4-b]pyridine 3-carboxylate product as residue. The residue is purified by chromatographing on silica gel using ethyl acetate-hexane as eluant.

Workup

  1. temperatureat reflux temperature for 90 minutes
  2. temperatureto cool
  3. washthe diluted solution washed with 2N hydrochloric acid and brine
  4. customdried
  5. customthe solvent then is evaporated

Sources & evidence

ORD record
ord-24ead489973b4b52bffd04ede8e9fa2c
Source dataset
uspto-grants-1986_01
Patent number
US04567268

Reaction notes

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