Hydrazine → HCID 19699095, compound

HRID 863020Notes

Reaction equation

HRID 863020 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[N:18][NH:19][C:13]=3[C:12]3[S:20][CH:21]=[CH:22][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[N:18][NH:19][C:13]=3[C:12]3[S:20][CH:21]=[CH:22][C:11]2=3)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 19699106HCID 19699106, compound

Product 1

HCID 19699095HCID 19699095, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.0 g of 6-(4-nitrobenzoyl)-1,4,5,6-tetrahydropyrazolo[3,4-d]thieno[3,2-b]azepine in 40 ml of absolute ethanol is stirred under argon while 1.6 ml of hydrazine is added. The reaction mixture is heated at 60° C. for 1.5 hours. The reaction mixture is cooled to room temperature and 400 mg of 10% Pd/C added and the reaction mixture heated at 100° C. for 1.5 hours. The reaction mixture is filtered through diatomaceous earth and the cake washed with methylene chloride. The filtrate is concentrated in vacuo to a residue which is crystallized from ethyl acetate:hexane to give 1.4 g of the desired product as yellow crystals, 242°-260° C.

Workup

  1. additionis added
  2. temperatureThe reaction mixture is cooled to room temperature
  3. temperaturethe reaction mixture heated at 100° C. for 1.5 hours
  4. filtrationThe reaction mixture is filtered through diatomaceous earth
  5. washthe cake washed with methylene chloride
  6. concentrationThe filtrate is concentrated in vacuo to a residue which
  7. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-57951aa35c194b3e9c080edd6d143dd6
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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