Hydrazine → HCID 22466726, compound

HRID 1934993Notes

Reaction equation

HRID 1934993 reaction equation
[CH3:1][O:2][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.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]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 22466687HCID 22466687, compound

Product 1

HCID 22466726HCID 22466726, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

325 mg of 10% palladium on carbon was added to a round bottom flask under N2 and covered with 165 ml ethanol. Added 3.29 g (10.3 mmol) 4-[(3-methoxyphenyl)amino]-6-nitro-3-quinolinecarbonitrile and 800 μl anhydrous hydrazine and heated mixture to reflux. At 1.5 hours, filtered hot through celite, stripped solvent and dried in vacuo, giving 2.876 g of yellow solid: mass spectrum (electrospray m/e): M+H=291.2.

Workup

  1. temperatureheated mixture
  2. temperatureto reflux
  3. filtrationfiltered hot through celite
  4. customdried in vacuo

Sources & evidence

ORD record
ord-280f187f72c14f24a0446c89b8327e3a
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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