Ethyl Acetate → 2-Amino-10,11-dihydro-dibenz[b,f]oxepin-10-one

HRID 437816Notes

Reaction equation

HRID 437816 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[O:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1)([O-])=O.C(OCC)(=O)C>[Pt]=O.C(O)C>[NH2:1][C:4]1[CH:19]=[CH:18][C:7]2[O:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 2276785510,11-Dihydro-2-nitro-dibenz[b,f]oxepin-10-one

Product 1

HCID 227679272-Amino-10,11-dihydro-dibenz[b,f]oxepin-10-one

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

52.5 G. of 10,11-dihydro-2-nitro-dibenz[b,f]oxepin-10-one are suspended in 900 ml. of ethyl acetate and 450 ml. of ethanol and hydrogenated in the presence of 300 mg. of platinum oxide at room temperature and normal pressure. The catalyst is removed by filtration, the filtrate evaporated in vacuo. The residue is crystallized from benzene/hexane, and there is obtained 2-amino-10,11-dihydro-dibenz[b,f]oxepin-10-one having a melting point of 116°-117° C.

Workup

  1. customat room temperature
  2. customThe catalyst is removed by filtration
  3. customthe filtrate evaporated in vacuo
  4. customThe residue is crystallized from benzene/hexane

Sources & evidence

ORD record
ord-2ea753e49db14aa782e102370bf193cf
Source dataset
uspto-grants-1977_06
Patent number
US04032525

Reaction notes

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