Pyridine → HCID 13193766, compound

HRID 1285548Notes

Reaction equation

HRID 1285548 reaction equation
C1C=C[NH+]=CC=1.Br[Br-]Br.C[C:11]1[NH:12][C:13]([CH3:34])=[C:14]([C:30]([O:32][CH3:33])=[O:31])[CH:15]([C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)[C:16]=1[C:17]([O:19][CH3:20])=[O:18].N1C=CC=CC=1>C(O)C>[CH3:34][C:13]1[NH:12][C:11]2[CH2:20][O:19][C:17](=[O:18])[C:16]=2[CH:15]([C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)[C:14]=1[C:30]([O:32][CH3:33])=[O:31]

Participants

4

Reactant 2

HCID 1049PyridineHCID 704243dimethyl 4-(1,3-benzodioxol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 13193766HCID 13193766, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In a similar manner, 2.78 grams (6.95 millimoles) of pyridinium bromide perbromide was added in one portion to a cooled to 0° C. mixture of 2 grams of dimethyl 2,6-dimethyl-4-(3,4-methylenedioxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.81 milliliter of pyridine in 40 milliliters of ethanol-free chloroform, the resulting mixture stirred at 0° C. for 30 minutes then heated at reflux temperature for 90 minutes to obtain a methyl 2-methyl-4-(3,4-methylenedioxyphenyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product in the reaction mixture. The product was recovered in a manner similar to that previously described and purified over silica with 70/30 ethyl acetate/hexane to obtain 740 milligrams (39 percent yield) of white crystals. An analytical sample having a melting point of 226°-228° C. was obtained by recrystallizing from ethyl acetate/hexane and drying at 80° C./0.005 millimeters Hg pressure for 48 hours. Elemental analyses were as follow:

Workup

  1. temperaturethen heated
  2. temperatureat reflux temperature for 90 minutes

Sources & evidence

ORD record
ord-3977b416761e41028cf5851373e29ec0
Source dataset
uspto-grants-1986_01
Patent number
US04567268

Reaction notes

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