Hydrochloric Acid → 3-(2-Chlorophenyl)-5-hydroxymethyl-1-phenyl-1,2-dihydropyridin-2-one

HRID 547683Notes

Reaction equation

HRID 547683 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:24])[N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=[C:12]([C:14](OC)=[O:15])[CH:13]=1.BrC1C(=O)N(C2C=CC=CC=2)C=C(C(OC)=O)C=1.Cl.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:24])[N:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:11]=[C:12]([CH2:14][OH:15])[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 223189503-Bromo-5-methoxycarbonyl-1-phenyl-1,2-dihydropyridin-2-oneHCID 223190963-(2-Chlorophenyl)-5-methoxycarbonyl-1-phenyl-1,2-dihydropyridin-2-one

Product 1

HCID 223189533-(2-Chlorophenyl)-5-hydroxymethyl-1-phenyl-1,2-dihydropyridin-2-oneYield 36.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

36 mg of 3-(2-chlorophenyl)-5-methoxycarbonyl-1-phenyl-1,2-dihydropyridin-2-one synthesized by the method of Referential Example 3 from 3-bromo-5-methoxycarbonyl-1-phenyl-1,2-dihydropyridin-2-one and 2-chloroboronic acid, was dissolved in 20 ml of toluene. After cooling to −78° C., 0.1 ml diisopropyl aluminumhydride (1.5M tetrahydrofuran solution) was added dropwise thereinto. While heating from −78° C. to room temperature, the mixture was stirred overnight. Then, 1N hydrochloric acid was added thereto, followed by stirring. The mixture was neutralized with an aqueous solution of sodium hydrogen carbonate, and then extracted with ethyl acetate. Then, the extract was successively washed with water and brine, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12 mg of the title compound.

Workup

  1. temperatureWhile heating from −78° C. to room temperature
  2. stirringby stirring
  3. extractionextracted with ethyl acetate
  4. washThen, the extract was successively washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThen, the solvent was evaporated
  7. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-837747d4f6a0470dae5a904f90b237ab
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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