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

HRID 2356866Notes

Reaction equation

HRID 2356866 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.ClC1C=CC=CC=1B(O)O.[H-].C([Al+]CC(C)C)C(C)C.Cl.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[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

8

Reactant 6

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 27343222-Chlorophenylboronic acidHCID 21225700DiisobutylaluminumhydrideHCID 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 1

HCID 1140TolueneSolvent

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-chlorophenylboronic acid, was dissolved in 20 ml of toluene. After cooling to −78° C., 0.1 ml diisobutyl aluminum hydride (1.5 M 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 titles compound.

Workup

  1. temperatureWhile heating from −78° C. to room temperature
  2. stirringby stirring
  3. extractionand then extracted 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-8e7d9165059b42f697b61c480533c5ca
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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