Tetrahydrofuran → Oxazolo(4,5-b)pyridin-2(3H)-one

HRID 1612785Notes

Reaction equation

HRID 1612785 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[O:9]1CCC[CH2:10]1>>[O:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[NH:1][C:10]1=[O:9]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 2799900Oxazolo(4,5-b)pyridin-2(3H)-one

Procedure

5.5 g (0.05 mol) of 2-amino-3-hydroxypyridine are introduced into a three-necked flask and the system is placed under argon. 100 ml of anhydrous tetrahydrofuran (THF) are added 12 15 g (0.075 mol) of 1,1-carbonyldiimidazole are then introduced. The mixture is heated to reflux for 5 hours (under argon) The THF is then evaporated off. The residue is taken up with dichloromethane. Washes of the organic phase are performed with NaOH solution (5%) (6 × 150 ml); the cyclized product passes into the aqueous phase and is precipitated at a pH in the region of 5 (by adding 2 N hydrochloric acid solution). The product is filtered off and stored in a desiccator.

Workup

  1. additionare then introduced
  2. temperatureThe mixture is heated
  3. customis then evaporated off
  4. customis precipitated at a pH in the region of 5 (by adding 2 N hydrochloric acid solution)
  5. filtrationThe product is filtered off
  6. customstored in a desiccator

Sources & evidence

ORD record
ord-b9e047f5f2034f26abd22eda1466b727
Source dataset
uspto-grants-1993_03
Patent number
US05190960

Reaction notes

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