Hydrazine → HCID 54166381, compound

HRID 355870Notes

Reaction equation

HRID 355870 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[C:4]([N:6]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=[O:5].NN>C(O)C.[Pd]>[Cl:1][C:2]1[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:3]=1[C:4]([N:6]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=[O:5]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 67626026HCID 67626026, compound

Product 1

HCID 54166381HCID 54166381, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.40 g of 5-(2-chloro-4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine, 0.20 g of 10% palladium-on-carbon, 0.25 g of anhydrous hydrazine in 25 ml of absolute ethanol is heated at reflux for 1 hour. The mixture is filtered through diatomaceous earth and the filtrate evaporated in vacuo to a residue which is dissolved in methylene chloride and hexane added at the boil to give 0.60 g of the desired product as a crystalline solid, m.p. 158°-161° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe mixture is filtered through diatomaceous earth
  4. customthe filtrate evaporated in vacuo to a residue which
  5. dissolutionis dissolved in methylene chloride
  6. additionhexane added at the boil

Sources & evidence

ORD record
ord-e20dad8c655c4b198b8a36fc42ffaabb
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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