HCID 22006209, compound → HCID 22006216, compound

HRID 323577Notes

Reaction equation

HRID 323577 reaction equation
[CH3:1][O:2][CH:3]([O:25][CH3:26])[C:4]1[NH:5][C:6]([CH:20]([O:23][CH3:24])[O:21][CH3:22])=[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:26][O:25][CH:3]([O:2][CH3:1])[C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:6]([CH:20]([O:23][CH3:24])[O:21][CH3:22])[N:5]=1

Participants

4

Reactant 1

HCID 22006209HCID 22006209, compound

Product 1

HCID 22006216HCID 22006216, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

To a solution of diethyl 2,6-bis[(dimethoxy)methyl]-1 ,4-dihydropyridine-3,5-dicarboxylate (3.40 g, 9.10 mmol) in toluene (200 ml) was added activated manganese dioxide (3.96 g, 45.5 mmol) and the resulting mixture was heated to reflux for 2 hours. At this time another 3.96 g (45.5 mmol) of activated manganese dioxide was added and reflux was continued an additional 2 hours. The reaction was allowed to cool to room temperature, filtered through celite, and concentrated to afford 3.10 g (92% yield) of diethyl 2,6-bis[(dimethoxy)methyl]-3,5-pyridine dicarboxylate as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 8.29 (s, 1 H), 5.93 (s, 2H), 4.40 (q, J=7.2 Hz, 4 H), 3.48 (s, 12 H), 1.41 (t, J=7.2 Hz, 6 H). 13C NMR (75 MHz, CDCl3) dc 165.68 (s), 156.25 (s), 138.52 (d), 126.59 (d), 101.26 (d), 61.50 (t), 54.08 (q), 13.75 (q). MS (LR-CI) m/z 372 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturereflux
  4. filtrationfiltered through celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4dd72013869a4b21b9874a82e81be41d
Source dataset
uspto-grants-2001_04
Patent number
US06214817B1

Reaction notes

Loading…