Hydrochloric Acid → 1,6-Dihydro-5-(4-methylphenyl)-1-methyl-3[2H]-pyridone

HRID 2166571Notes

Reaction equation

HRID 2166571 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Mg]Br)=[CH:3][CH:2]=1.CO[C:12]1[CH2:17][N:16]([CH3:18])[CH2:15][C:14](=[O:19])[CH:13]=1.CO.Cl>CCOCC.C1COCC1>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([C:12]2[CH2:17][N:16]([CH3:18])[CH2:15][C:14](=[O:19])[CH:13]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 129007045-methoxy-1-methyl-1,6-dihydropyridin-3(2H)-oneHCID 178418370HCID 178418370, compound

Product 1

HCID 204998011,6-Dihydro-5-(4-methylphenyl)-1-methyl-3[2H]-pyridone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-tolyl magnesium bromide (0.23 M) in ether (150 ml) was treated with a solution of 5-methoxy-1-methyl-1,6-dihydro-3[2H]pyridone (28.2 g, 0.2 M) in THF (200 ml) at such a rate as to maintain a gentle reflux. After 1 hour the reaction mixture was poured on to methanol (500 ml) and treated with 12 N hydrochloric acid (50 ml). Removal of the resulting crystals by filtration followed by air-drying gave the title compound (21 g) as the hydrochloride five quarters hydrate.

Workup

  1. temperatureto maintain a gentle reflux
  2. customRemoval of the resulting crystals
  3. filtrationby filtration
  4. customby air-drying

Sources & evidence

ORD record
ord-219c716097474efcafbbb9c8c3e2d803
Source dataset
uspto-grants-1983_06
Patent number
US04387230

Reaction notes

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