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

HRID 742212

Reaction equation

HRID 742212 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 triectylorthopropionate is removed in vacuo and the resulting oil is purified by column chromatography. The tractions containing the pure desired product are combined and stripped 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 triectylorthopropionate 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-4152acb833df48aa92d0b5c528c00c32
Source dataset
uspto-grants-1996_09
Patent number
US05554579

Linked notes

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