Hydrazine → HCID 22466682, compound

HRID 1935150Notes

Reaction equation

HRID 1935150 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:24]#[N:25])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].NN>[Pd].C(O)C>[NH2:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:24]#[N:25])=[C:11]2[NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 22466539HCID 22466539, compound

Product 1

HCID 22466682HCID 22466682, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Added 0.5 g 10% palladium on carbon to a flask under N2 and covered with 250 ml ethanol. To this added 4.818 g (14.5 mmol) 4-[(3-isopropylphenyl)amino]-6-nitro-3-quinolinecarbonitrile and 1.14 ml (36.2 mmol) anhydrous hydrazine and heated to reflux. At 1.5 hours, filtered hot mixture through celite, stripped solvent, and dried in vacuo, giving 4.30 g of yellow solid: mass spectrum (electrospray m/e): M+H=303.1.

Workup

  1. filtrationfiltered hot mixture through celite
  2. customdried in vacuo

Sources & evidence

ORD record
ord-8305f0a92eaa4405a4df524dc6dc22e7
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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