HCID 20272886, compound → HCID 13242128, compound

HRID 371420Notes

Reaction equation

HRID 371420 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:30])=[C:5](C([O-])=O)[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(O)COCCO.CCOCC.O>[CH3:1][C:2]1[NH:3][C:4]([CH3:30])=[CH:5][CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 20272886HCID 20272886, compound

Product 1

HCID 13242128HCID 13242128, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 8117Diethylene GlycolSolventHCID 21584184Diethylether waterSolvent

Procedure

3 g of monomethyl 1,4-dihydro-2,6-dimethyl-4-[2-(4-methylbenzyloxy)-phenyl]-pyridine-3,5-dicarboxylate were suspended in 30 ml of diethylene glycol, and the suspension was heated to 170° to 180° C. while stirring, a clear solution being formed with evolution of gas. The mixture was stirred for approx. 5 minutes at 180° C., and was cooled. The viscous solution was dissolved in an ether/water mixture with vigorous shaking, the mixture was separated, the aqueous phase was extracted with ether, and the combined ether phases were washed with 1N sodium hydroxide solution and twice with water. The ether phase was dried, filtered and concentrated. The resulting syrupy residue was crystallized in an ice-bath, using isopropanol or acetonitrile, and the crystals were filtered off under suction. 1.6 g of methyl 1,4-dihydro-2,6-dimethyl-4-[2-(4-methylbenzyloxy)-phenyl]-pyridine-3-carboxylate of melting point 107° C. to 109° C. were obtained.

Workup

  1. temperaturethe suspension was heated to 170° to 180° C.
  2. customa clear solution being formed with evolution of gas
  3. stirringThe mixture was stirred for approx. 5 minutes at 180° C.
  4. temperaturewas cooled
  5. customthe mixture was separated
  6. extractionthe aqueous phase was extracted with ether
  7. washthe combined ether phases were washed with 1N sodium hydroxide solution and twice with water
  8. dry with materialThe ether phase was dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting syrupy residue was crystallized in an ice-bath
  12. filtrationthe crystals were filtered off under suction

Sources & evidence

ORD record
ord-d0f55360de324dd39766de4399e632b0
Source dataset
uspto-grants-1985_07
Patent number
US04532248

Reaction notes

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