Hydrochloric Acid → HCID 19704912, compound

HRID 726960Notes

Reaction equation

HRID 726960 reaction equation
CO[C:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:5](=[O:15])[CH:4]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O>[NH:16]([C:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:5](=[O:15])[CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 107506631H-1-Benzazepine-2,5-dione, 3-methoxy-

Product 1

HCID 19704912HCID 19704912, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (1.0 g) and aniline (10 mL) were heated to reflux for 5 hours and diluted with water. Hydrochloric acid (2N) was added and the mixture extracted with ethyl acetate. The organic extracts were washed (acid, brine), dried and evaporated to give a solid which was purified by chromatography, with ethyl acetate:toluene (1:4) as the eluent. Recrystallization from ethyl acetate gave the title compound (0.405 g); mp 227°-228° C.: NMR: 6.28 (s,1); MS(EI): m/z=264(M). Analysis for C16H12N2O2.0.1 H2O : Calculated: C, 72.22; H, 4.62; N, 10.53; Found: C, 72.32; H, 4.68; N, 10.65.

Workup

  1. temperatureto reflux for 5 hours
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic extracts were washed (acid, brine)
  4. customdried
  5. customevaporated
  6. customto give a solid which
  7. customwas purified by chromatography, with ethyl acetate:toluene (1:4) as the eluent
  8. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ceb11b016a2644328ee631a5d091a98d
Source dataset
uspto-grants-1998_01
Patent number
US05712272

Reaction notes

Loading…