Pyridine → HCID 13193770, compound

HRID 1285551Notes

Reaction equation

C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:10][C:11]1[NH:12][C:13](C)=[C:14]([C:29]([O:31][CH3:32])=[O:30])[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[C:16]=1[C:17]([O:19][CH3:20])=[O:18].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:10][C:11]1[NH:12][C:13]2[CH2:32][O:31][C:29](=[O:30])[C:14]=2[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

In a manner similar to that described in the preceding examples, 1.45 grams of 80 percent pyridinium bromide perbromide was added to a cooled to 0° C. solution of 1.00 gram (3.02 millimoles) of dimethyl 2,6-dimethyl-4(2-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.40 milliliter of pyridine in 20 milliliters of chloroform. The mixture was then stirred at 0° C. for about 30 minutes and at reflux temperature for about 90 minutes. Thereafter the mixture was allowed to cool, diluted with chloroform, washed with 2N hydrochloric acid and brine, dried and the solvent evaporated to obtain a crude product residue. The latter was flash chromatographed on 35 grams of silica gel to obtain 510 milligrams (54 percent yield) of purified methyl 2-methyl-4-(2-methoxyphenyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product. A portion of the product was recrystallized from ethyl acetate-hexane for elemental analyses which were as follows:

Workup

additionwas added to
temperatureat reflux temperature for about 90 minutes
temperatureto cool
washwashed with 2N hydrochloric acid and brine
customdried
customthe solvent evaporated
customto obtain a crude product residue
customchromatographed on 35 grams of silica gel

Sources & evidence

ORD record: ord-cf342350532340978fd8401848151eb0
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04567268

Reaction notes

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