D-Psicose → Ethyl 3,5-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxylate

HRID 52434Notes

Reaction equation

HRID 52434 reaction equation
C([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[C:10]([CH3:16])=[C:9]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])C1C=CC=CC=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C(O)(=O)C>[CH2:20]([O:19][C:17]([C:9]1[NH:8][CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[C:10]=1[CH3:16])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 441036D-PsicoseHCID 11781103HCID 11781103, compound

Product 1

HCID 11745550Ethyl 3,5-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of pyridone 5 (5.1 g, 17.89 mmol) in acetic acid (100 ml) was added 10% Pd--C (0.2 g), and the reaction mixture was hydrogenated (55 Psi) at room temperature overnight. The mixture was then filtered through Celite and the filtrate was evaporated. The residue was thoroughly washed with 10% potassium carbonate, water and dried in vacuo to give compound 6 as a white powder (3.3 g, 95% yield) m.p. 124°-126° C. 1H-NMR (DMSO-d6) δ 7.52 (brs, 1H), 4.45 (q, J=7.2 Hz, 2H), 2.40 (s, 3H), 2.07 (s, 3H), 1.42(t, J=7.2 Hz, 3H). Ms(13eV)m/z(%): 195.0(M+, 100), 165.9(40), 148.9(50), 122.9(80), 121.0(100). Anal. Calcd for C10H13NO3 : C, 61.53; H, 6.71; N, 7.18. Found: C, 61.48; H, 6.63; N, 7.09.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe mixture was then filtered through Celite
  4. customthe filtrate was evaporated
  5. washThe residue was thoroughly washed with 10% potassium carbonate, water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-92964bc37979441d9ab07e7adaca2a6f
Source dataset
uspto-grants-1997_04
Patent number
US05616713

Reaction notes

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