Ammonia → HCID 19704915, compound

HRID 726957Notes

Reaction equation

HRID 726957 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[CH:4]=[C:3]1OC.[NH3:16]>CO>[NH2:16][C:3]1[C:2](=[O:1])[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 107506631H-1-Benzazepine-2,5-dione, 3-methoxy-

Product 1

HCID 19704915HCID 19704915, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

2,5-Dihydro-2,5-dioxo-3-methoxy-1H-benz[b]azepine (0.4 g) was treated with 80 mL of liquid anhydrous ammonia chilled to -78° C. The mixture was sealed in a pressure vessel and warmed to 23° C. for 18 hours. The excess ammonia was evaporated to give a solid. The solid was dissolved in hot methanol (120 mL); the solution was filtered and evaporated to 60 mL; and crystallization was initiated by cooling the solution in an ice bath. The solid was filtered, washed (cold methanol) and dried under vacuum (25° C., 15 Pa) to give the title compound (0.28 g); mp 295.2°-296.5° C. (dec); NMR: 11.38 (s,1, NH), 8.09 (dd,1, J=8.2, 1.6), 7.54 (m,1), 7.44 (dd,1, J=8.2, 1.6), 7.21 (m,1), 6.23 (s,1). Analysis for C10H8N2O2 : Calculated: C, 63.82; H, 4.28; N, 14.89; Found: C, 63.80; H, 4.41; N, 14.87.

Workup

  1. customThe mixture was sealed in a pressure vessel
  2. temperaturewarmed to 23° C. for 18 hours
  3. customThe excess ammonia was evaporated
  4. customto give a solid
  5. filtrationthe solution was filtered
  6. customevaporated to 60 mL
  7. customand crystallization
  8. temperatureby cooling the solution in an ice bath
  9. filtrationThe solid was filtered
  10. washwashed (cold methanol)
  11. customdried under vacuum (25° C., 15 Pa)

Sources & evidence

ORD record
ord-baecf969b87c41e0a7a2ceac15847830
Source dataset
uspto-grants-1998_01
Patent number
US05712272

Reaction notes

Loading…