p-Toluenesulfonic acid → Diethyl 2-ethyloxazolo[5,4-b]pyridine-5,6-dicarboxylate

HRID 54185

Reaction equation

HRID 54185 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=1.C(O[C:22](OCC)(OCC)[CH2:23][CH3:24])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:23]([C:24]1[O:8][C:7]2[C:2]([N:1]=1)=[CH:3][C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]=2)[CH3:22]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 66995Ethyl orthopropionateHCID 19958246Diethyl 5-amino-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Product 1

HCID 19958240Diethyl 2-ethyloxazolo[5,4-b]pyridine-5,6-dicarboxylateYield 84.8%

Procedure

Diethyl 5-amino-1,6-dihydro-6-oxo-pyridine-2,3-dicarboxylate (7.57 g, 0.030 mol), is suspended in 60 mL triethylorthopropionate (TEOP 0.30 mol). A small amount of p-toluenesulfonic acid is added and the mixture is heated at reflux for 65 hours. The triethyorthopropionate is removed in vacuo and the resulting oil is purified by column chromatography. The tractions containing the pure desired product are combined and striped to a honey-colored oil weighing 7.38 g, yield 84.8%.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 65 hours
  3. customThe triethyorthopropionate is removed in vacuo
  4. customthe resulting oil is purified by column chromatography
  5. additionThe tractions containing the pure desired product

Sources & evidence

ORD record
ord-617c5dc0849b4bb4b694c4bee7c154cd
Source dataset
uspto-grants-1997_04
Patent number
US05622913

Linked notes

Loading…