Hydrazine → HCID 10062179, compound

HRID 326880Notes

Reaction equation

HRID 326880 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[C:5]2[NH:11][CH2:10][CH2:9][N:8]([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH:7]([CH3:17])[C:6]=2[CH:18]=1.NN>CO.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:19])[C:5]2[NH:11][CH2:10][CH2:9][N:8]([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH:7]([CH3:17])[C:6]=2[CH:18]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 10425462HCID 10425462, compound2×

Product 1

HCID 10062179HCID 10062179, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 1.34 parts of 7-chloro-2,3,4,5-tetrahydro-5-methyl-4-(3-methyl-2-butenyl)-9-nitro-1H-1,4-benzodiazepine (prepared as intermediate 11) in methanol there were added 0.49 parts of Raney nickel. To the resulting suspension there was added dropwise a solution of 1.09 parts of hydrazine in a small amount of methanol, at reflux temperature and under an Argon atmosphere. Refluxing was continued for 11/2 hour. After cooling, the catalyst was filtered off and the filtrate was evaporated, yielding 1.3 parts (100%) of 7-chloro-2,3,4,5-tetrahydro-5-methyl-4-(3-methyl-2-butenyl)-1H-1,4-benzodiazepin-9-amine (interm. 19).

Workup

  1. temperatureat reflux temperature
  2. temperatureRefluxing
  3. custom2 hour
  4. temperatureAfter cooling
  5. filtrationthe catalyst was filtered off
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9158063fa4a448a2b10f9c25f253b9bb
Source dataset
uspto-grants-1993_12
Patent number
US05270464

Reaction notes

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