Water → Methyl 5-acetyl-4-(4-chlorophenyl)-1,2,6-trimethyl-1,4-dihydropyridine-3-carboxylate

HRID 263975Notes

Reaction equation

[C:1]([C:4]1[CH:5]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:6]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[H-].[Na+].[CH3:25]I.O>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:4]1[CH:5]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:6]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:11])[N:8]([CH3:25])[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1.0 g (3.2 mmol) of the compound from Example I are dissolved in 15 ml of DMF and treated under argon with 180 mg of NaH. The mixture is stirred at 0° C. for 15 minutes. 0.51 ml (6.2 mmol) of MeI is then added dropwise and the mixture is stirred again for 30 min. It is treated successively with H2O and ethyl acetate and the organic phase is washed with saturated aqueous NaCl solution. It is then concentrated and the residue is separated on silica gel (petroleum ether/AcOEt=1+1). The appropriate fractions crystallize from Et2O/petroleum ether. 230 mg of the title compound are obtained. MS:333.8 Rf =0.57 (petroleum ether/AcOEt=1+1)

Workup

stirringthe mixture is stirred again for 30 min
washthe organic phase is washed with saturated aqueous NaCl solution
concentrationIt is then concentrated
customthe residue is separated on silica gel (petroleum ether/AcOEt=1+1)
customThe appropriate fractions crystallize from Et2O/petroleum ether

Sources & evidence

ORD record: ord-fec82b764d824a10bfd5fcdc33f0039a
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646166

Reaction notes

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