Pyridine → HCID 13193764, compound

HRID 1285546Notes

Reaction equation

HRID 1285546 reaction equation
C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:10][C:11]1[NH:12][C:13](C)=[C:14]([C:27]([O:29][CH3:30])=[O:28])[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]=1[C:17]([O:19][CH3:20])=[O:18].N1C=CC=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH3:10][C:11]1[NH:12][C:13]2[CH2:30][O:29][C:27](=[O:28])[C:14]=2[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 2

HCID 1049PyridineHCID 129839Dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 13193764HCID 13193764, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

1.58 grams of 80 percent pyridinium bromide perbromide (3.95 millimoles) was added in one portion to a cooled to 0° C. solution of 1.00 gram (3.32 millimoles) of dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.4 milliliter of pyridine in 20 milliliters of dry ethanol-free chloroform. The resulting mixture was stirred for 45 minutes at 0° C. and then heated at reflux temperature for 1.3 hous. Thereafter, the mixture was cooled to room temperature, diluted with chloroform and the resulting solution washed successively with 2N hydrochloric acid and brine, dried over magnesium sulfate, and dried solution filtered to remove the drying agent, and then subjected to reduce pressure to vaporize the solvent and to recover as residue 1.41 grams of product as a yellow oil. The oil was chromatographed on silica gel using 70 percent ethyl acetate--30 percent hexane as eluant to obtain 595 milligrams (63 percent yield) of purified methyl 2-methyl-4-phenyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]-pyridine-3-carboxylate product which after recrystallization from ethyl acetate-hexane and drying at 60° C. at 0.005 millimeters mercury pressure for 17 hours had a melting point of 193°-196° C. Elemental analyses for the product were as follows:

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1.3 hous
  3. temperatureThereafter, the mixture was cooled to room temperature
  4. washthe resulting solution washed successively with 2N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate, and dried solution
  6. filtrationfiltered
  7. customto remove the drying agent
  8. customto recover as residue 1.41 grams of product as a yellow oil
  9. customThe oil was chromatographed on silica gel using 70 percent ethyl acetate--30 percent hexane as eluant

Sources & evidence

ORD record
ord-d24751920ecc4ab0b1594719c281d0e0
Source dataset
uspto-grants-1986_01
Patent number
US04567268

Reaction notes

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