Hydrazine → 5-(4-Amino-3-methylbenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 2293196Notes

Reaction equation

HRID 2293196 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH2:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:6][C:5]=1[CH3:27])([O-])=O.NN>[Pd].C(O)C>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH2:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:6][C:5]=1[CH3:27]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 54506243HCID 54506243, compound

Product 1

HCID 540843085-(4-Amino-3-methylbenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineYield 78.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.11 g of 5-(4-nitro-3-methylbenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine, 50 ml of ethanol, 0.30 g of anhydrous hydrazine and 0.27 g palladium-on-carbon is refluxed 1 hour, and then filtered through diatomaceous earth. The filtrate is evaporated and the residue recrystallized from dichloromethane-hexane to give 0.80 g of crystals, m.p. 203°-204° C.

Workup

  1. temperatureis refluxed 1 hour
  2. filtrationfiltered through diatomaceous earth
  3. customThe filtrate is evaporated
  4. customthe residue recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-34cb77855729416297875190acb765ea
Source dataset
uspto-grants-1997_11
Patent number
US05686445

Reaction notes

Loading…