Pyridine → HCID 18679322, compound

HRID 1633504Notes

Reaction equation

HRID 1633504 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])O[C:8](=[O:9])[C:7]=12.[N:14]1C=CC=C[CH:15]=1>C(O)(=O)C>[CH3:1][C:2]1[C:7]2[C:8](=[O:9])[NH:14][CH2:15][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 18679322HCID 18679322, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-Methylisatoic anhydride (10.0 g, 56 mmol) ethyl glycinate hydrochloride (9.77g, 1.25 equiv.) and anhydrous pyridine (200 mL) were combined and heated under reflux 3.5 h in a nitrogen atmosphere. The pyridine was removed by evaporation under reduced pressure to give an oil. The oil was dissolved in acetic acid (15 mL) and heated under reflux for 6 h. The volatiles were removed under reduced pressure to give a residue which was triturated methanol and filtered to recover 3.63 g of 6-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione as a yellow solid. The methanol filtrate was evaporated and acetic acid (200 mL) was added to the residue. The brown solution was heated under reflux overnight. The reaction mixture was cooled and the volume of acetic acid was reduced to half its volume under reduced pressure. Upon cooling, a solid precipitated which was collected. A second crop of 6-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (4.7 g) was obtained as a beige solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux 3.5 h in a nitrogen atmosphere
  3. customThe pyridine was removed by evaporation under reduced pressure
  4. customto give an oil
  5. temperatureheated
  6. temperatureunder reflux for 6 h
  7. customThe volatiles were removed under reduced pressure
  8. customto give a residue which
  9. customwas triturated methanol
  10. filtrationfiltered
  11. customto recover 3.63 g of 6-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione as a yellow solid
  12. customThe methanol filtrate was evaporated
  13. additionacetic acid (200 mL) was added to the residue
  14. temperatureThe brown solution was heated
  15. temperatureunder reflux overnight
  16. temperatureThe reaction mixture was cooled
  17. temperatureUpon cooling
  18. customa solid precipitated which
  19. customwas collected

Sources & evidence

ORD record
ord-4ab09bb6aae441038e85acd54cb7be0d
Source dataset
uspto-grants-2003_01
Patent number
US06503900B2

Reaction notes

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