HCID 70453253, compound → HCID 13560807, compound

HRID 1285554Notes

Reaction equation

HRID 1285554 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][CH2:32]CO)=[O:30])[CH:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]=1[C:17]([O:19][CH2:20][CH2:21][OH:22])=[O:18]>C(Cl)CCl.N1C=CC=CC=1>[CH3:10][C:11]1[NH:12][C:13]2[CH2:32][O:31][C:29](=[O:30])[C:14]=2[CH:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]=1[C:17]([O:19][CH2:20][CH2:21][OH:22])=[O:18]

Participants

4

Reactant 1

HCID 70453253HCID 70453253, compound

Product 1

HCID 13560807HCID 13560807, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2.33 grams of 80 percent pyridinium bromide perbromide (1.46 millimoles) was added to a solution of 500 milligrams (1.51 millimoles) of bis(2-hydroxyethyl) 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate in 400 milliliters of ethylene dichloride and 1.6 milliliters of pyridine. The resulting mixture was stirred at 0° C. for 1 hour and then heated at reflux temperature for 2 hours. Thereafter, the mixture was cooled to room temperature, the resulting solution washed with 2N hydrochloric acid, sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered, and the filtrate subjected to reduced pressure to vaporize the solvent and to recover as residue a semi-crystalline solid. The solid was not crystallizable from acetonitrile. The acetonitrile was vaporized to obtain an orange oil which on trituration with ethyl acetate produced crystals. The crystals, after recrystallization twice from ethyl acetate, had a melting point of 185°-186° C. 1H NMR and elemental analyses showed the product to have ethyl acetate solvate of crystallization. Elemental analyses were as follows:

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThereafter, the mixture was cooled to room temperature
  4. washthe resulting solution washed with 2N hydrochloric acid, sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customto recover as residue a semi-crystalline solid
  8. customto obtain an orange oil which on trituration with ethyl acetate produced crystals
  9. customThe crystals, after recrystallization twice from ethyl acetate
  10. customethyl acetate solvate of crystallization

Sources & evidence

ORD record
ord-91e2ee46445746918a7b213289d95db0
Source dataset
uspto-grants-1986_01
Patent number
US04567268

Reaction notes

Loading…