Ammonia → 3-Amino-8-chloro-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

HRID 2396461Notes

Reaction equation

HRID 2396461 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]=[C:9](OC)[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1.[NH3:17]>>[NH2:17][C:9]1[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[C:11](=[O:12])[CH:10]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 150296358-Chloro-3-methoxy-1H-1-benzazepine-2,5-dione

Product 1

HCID 197049003-Amino-8-chloro-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Conditions

Temperature
-78 °C

Procedure

8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro-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 26° C. for 22.5 hours. The excess ammonia was evaporated to give a solid. The solid was recrystallized from 5 mL hot dimethylformamide and water; crystallization was initiated by cooling the solution in an ice bath. The solid was filtered, washed (water) and vacuum dried (100 ° C., 15 Pa) to give the title compound (0.274 g); mp 44.5-346.4 ° C. (dec); NMR: 11.47 (s,1), 8.10 (d,1, J=8.7), 7.53 (d,1, J=2.0), 7.27 (dd,1, 3=8.7, 2.0), 7.1 (broad s,2, NH2), 6.23 (s,1). Analysis for C10H7ClN2O2 : Calculated: C, 53.95; H, 3.17 ; N, 12.58; Found: C, 53.80; H, 3.34; N, 12.89.

Workup

  1. customThe mixture was sealed in a pressure vessel
  2. temperaturewarmed to 26° C. for 22.5 hours
  3. customThe excess ammonia was evaporated
  4. customto give a solid
  5. customThe solid was recrystallized from 5 mL hot dimethylformamide and water
  6. customcrystallization
  7. temperatureby cooling the solution in an ice bath
  8. filtrationThe solid was filtered
  9. washwashed (water) and vacuum
  10. customdried (100 ° C., 15 Pa)

Sources & evidence

ORD record
ord-e22ffdfed8dc47028873980d83331f5f
Source dataset
uspto-grants-1996_02
Patent number
US05492905

Reaction notes

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