Hydrochloric Acid → HCID 66734647, compound

HRID 1963113Notes

Reaction equation

HRID 1963113 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[CH2:9]([Mg]Cl)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl[C:20]([O:22][CH3:23])=[O:21].Cl>C1COCC1>[O:2]=[C:3]1[CH:8]=[CH:7][N:6]([C:20]([O:22][CH3:23])=[O:21])[CH:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 692784-MethoxypyridineHCID 178418865HCID 178418865, compound

Product 1

HCID 66734647HCID 66734647, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

4-Methoxypyridine (9.30 mL, 91.64 mmol) was dissolved in THF (150 mL) under nitrogen atmosphere and cooled to −15° C. Phenethylmagnesium chloride (93 mL, 93.47 mmol, 1 M in THF) was added dropwise and a suspension was formed. After stirring at −20° C. for 30 minutes methyl chloroformate (9.23 mL, 119.13 mmol) was added over 1 minute. Stirring was continued at −10° C. for 1 h and then HCl (10%) was added. The mixture was stirred for 20 minutes and then concentrated. The aqueous phase was extracted with ether (×2) and the organic phase was dried (MgSO4) and evaporated to yield methyl 4-oxo-2-phenethyl-3,4-dihydropyridine-1(2H)-carboxylate (21.7 g, 82%) as an oil. 1H NMR (600 MHz, cdcl3) δ 1.98 (m, 2H), 2.54 (m, 2H), 2.69 (m, 1H), 2.81 (m, 1H), 3.83 (s, 3H), 4.62 (m, 1H), 5.33 (m, 1H), 7.12-7.38 (m, 5H), 7.72 (m, 1H); MS m/z 260 (M+H)+.

Workup

  1. customa suspension was formed
  2. additionwas added over 1 minute
  3. stirringThe mixture was stirred for 20 minutes
  4. concentrationconcentrated
  5. extractionThe aqueous phase was extracted with ether (×2)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-83b995f4a1ed4798ae197a5613e405ca
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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