1,1'-Carbonyldiimidazole → 5-Methyloxazolo[4,5-b]pyridin-2(3H)-one

HRID 1091013Notes

Reaction equation

HRID 1091013 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>O1CCCC1>[CH3:9][C:4]1[N:3]=[C:2]2[NH:1][C:10](=[O:11])[O:8][C:7]2=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 885002-Amino-6-methylpyridin-3-ol

Product 1

HCID 100120755-Methyloxazolo[4,5-b]pyridin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.24 g (10 mmol) of 2-amino-3-hydroxy-6-methylpyridine are introduced into a three-necked round-bottomed flask. The system is placed under argon. 20 ml of anhydrous tetrahydrofuran and then 2.43 g (15 mmol) of 1,1'-carbonyldimidazole are added. The mixture is heated to reflux for 6 hours. The reaction medium is evaporated. The crystals obtained are washed with water, filtered off and redissolved in hot methanol. The solution is filtered and re-evaporated.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 6 hours
  3. customThe reaction medium is evaporated
  4. customThe crystals obtained
  5. washare washed with water
  6. filtrationfiltered off
  7. dissolutionredissolved in hot methanol
  8. filtrationThe solution is filtered
  9. customre-evaporated

Sources & evidence

ORD record
ord-f921be403b2845559437f219e4688eab
Source dataset
uspto-grants-1992_01
Patent number
US05084456

Reaction notes

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