Hydrazine → HCID 9878960, compound

HRID 1935014Notes

Reaction equation

HRID 1935014 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:6]=[CH:7][CH:8]=1)#[N:2].NN>[Pd].C(O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([C:23]#[N:24])=[C:10]2[NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 9858039HCID 9858039, compound

Product 1

HCID 9878960HCID 9878960, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Added 100 mg of 10% palladium on carbon to a round bottom flask under N2 and covered with 50 ml ethanol. Added 1.00 g (3.17 mmol) 4-[(3-cyanophenyl)amino]-6-nitro-3-quinolinecarbonitrile and 250 μl (7.39 mmol) anhydrous hydrazine and heated to reflux. Removed heat at 2 hours and filtered hot through celite. Stripped solvent and dried in vacuo, giving 887 mg of yellow solid: mass spectrum (electrospray m/e): M+H=286.2.

Workup

  1. temperatureheated to reflux
  2. customRemoved
  3. temperatureheat at 2 hours
  4. filtrationfiltered hot through celite
  5. customdried in vacuo

Sources & evidence

ORD record
ord-447987aaa7704983a87c4d342e9389eb
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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