Pyridine → Methyl 1,4,5,7-tetrahydro-2-methyl-4-(2-methylphenyl)-5-oxofuro[3,4-b]pyridine-3-carboxylate

HRID 1285547Notes

Reaction equation

HRID 1285547 reaction equation
C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:10][C:11]1[NH:12][C:13]([CH3:32])=[C:14]([C:28]([O:30][CH3:31])=[O:29])[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:16]=1[C:17]([O:19]C)=[O:18].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:32][C:13]1[NH:12][C:11]2[CH2:10][O:19][C:17](=[O:18])[C:16]=2[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:14]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 1049PyridineHCID 12640525HCID 12640525, compound

Product 1

HCID 13193765Methyl 1,4,5,7-tetrahydro-2-methyl-4-(2-methylphenyl)-5-oxofuro[3,4-b]pyridine-3-carboxylateYield 61.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

In an operation carried out in a manner similar to that described in the preceding example, 1.52 grams of 80 percent pyridinium bromide perbromide (3.81 millimoles) was added in one portion to a solution of 1.00 gram (3.17 millimoles) of dimethyl 2,6-dimethyl-4-(o-tolyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.40 milliliter of pyridine in 20 milliliters of dry chloroform cooled to 0° C. The mixture was stirred for 30 minutes at 0° C., then at reflux temperature for 1.5 hours. Thereafter, the mixture was cooled, washed successively with hydrochloric acid and brine, dried, subjected to reduced pressure to remove the solvent and to obtain as residue crude methyl 2-methyl-4-(o-tolyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product. The crude product was chromatographed on silica and eluted with 65 percent ethyl acetate--35 percent hexane to obtain 0.58 gram (61 percent yield) of white crystalline material which after recrystallizing from ethyl acetate-hexane and drying at 80° C./0.005 mm Hg for 17 hours had a melting point of 224°-225° C. and the following analyses:

Workup

  1. temperatureat reflux temperature for 1.5 hours
  2. temperatureThereafter, the mixture was cooled
  3. washwashed successively with hydrochloric acid and brine
  4. customdried
  5. customto remove the solvent
  6. customto obtain as residue crude methyl 2-methyl-4-(o-tolyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product
  7. customThe crude product was chromatographed on silica
  8. washeluted with 65 percent ethyl acetate--35 percent hexane

Sources & evidence

ORD record
ord-b4ea088eeac2446daafb45077cc301f8
Source dataset
uspto-grants-1986_01
Patent number
US04567268

Reaction notes

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