Hydrochloric Acid → benzyl 4-oxo-2-phenyl-3,4-dihydropyridine-1(2H)-carboxylate

HRID 1437450Notes

Reaction equation

HRID 1437450 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.CO[C:11]1[CH:12]=[C:13]([Mg]Br)[CH:14]=[CH:15][CH:16]=1.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].Cl>C1COCC1>[O:2]=[C:3]1[CH:8]=[CH:7][N:6]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH:5]([C:16]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 692784-MethoxypyridineHCID 178490745HCID 178490745, compound

Product 1

HCID 10267212benzyl 4-oxo-2-phenyl-3,4-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

4-Methoxypyridine (1-1, 0.7 g, 6.4 mmol) in anhydrous THF at −20° C. was treated with 3-methoxyphenyl magnesium bromide (14.1 mL, 7.0 mmol) and benzyl chloroformate (1.09 g, 6.4 mmol) and stirred 4 h at −20° C. The reaction was poured into 1N HCl and stirred 10 min. The reaction mixture was extracted with Et2O (50 mL), washed with brine and dried over MgSO4. The organic extracts were filtered, concentrated under reduced pressure and purified viaflash column chromatography (SiO2, 0-50% EtOAc-hexanes gradient) to give benzyl 4-oxo-2-phenyl-3,4-dihydropyridine-1(2H)-carboxylate (1-2). MS 338.1 found 338.4 (M+H+) required.

Workup

  1. stirringstirred 10 min
  2. extractionThe reaction mixture was extracted with Et2O (50 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe organic extracts were filtered
  6. concentrationconcentrated under reduced pressure
  7. custompurified viaflash column chromatography (SiO2, 0-50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-b73a4ba8b3f847c48863ae313ec14773
Source dataset
uspto-grants-2009_11
Patent number
US07622489B2

Reaction notes

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