Ethyl 4-(6-oxo-1,6-dihydropyridin-3-yl)benzoate → HCID 18617476, compound

HRID 1264241Notes

Reaction equation

HRID 1264241 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH:4]=[CH:3]1>CC(O)=O>[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 18617564Ethyl 4-(6-oxo-1,6-dihydropyridin-3-yl)benzoate

Product 1

HCID 18617476HCID 18617476, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 4-(6-oxo-1,6-dihydro-pyridin-3-yl)-benzoate (450 mg, 1.8 mmol) (reference example 36f) is dissolved in HOAc (15 mL), and the the solution is degassed several times by alternating N2/vacuum. 50 mg of PtO2 is added and the mixture is degassed for several minutes before being placed under a H2 atmosphere. The mixture is stirred at room temperature for 9 hours then degassed several times by alternating N2/vacuum then filtered through a plug of celite. The plug is washed thoroughly with HOAc and the filtrate concentrated. The residue is chromatographed first on silica gel (3% MeOH/CH2Cl2), and then by Reverse-Phase HPLC to afford 330 mg of the title compound (72%) as a white solid. 1H NMR (CDCl3) δ 1.39 (t, J=7 Hz, 3H), 2.12 (m, 2H), 2.56 (m, 2H), 3.13 (m, 1H), 3.41 (dd, J=11.3, 11.3, 1H), 3.53 (m, 1H), 4.37 (q, J=7, 2H), 6.78 (bs, 1H), 7.16 (d, J=8 Hz, 2H), 8.01 (d, J=8 Hz, 2H). MS (Ion spray) m/z 248 (M+H)+.

Workup

  1. customthe the solution is degassed several times
  2. addition50 mg of PtO2 is added
  3. customthe mixture is degassed for several minutes
  4. customthen degassed several times
  5. filtrationthen filtered through a plug of celite
  6. washThe plug is washed thoroughly with HOAc
  7. concentrationthe filtrate concentrated
  8. customThe residue is chromatographed first on silica gel (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-185489f366a24404a13edd9afa51747a
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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