Hydrazine → 6-Amino-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrile

HRID 612070Notes

Reaction equation

HRID 612070 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]#[N:15])=[C:7]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1)([O-])=O.NN>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]#[N:15])=[C:7]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 224665426-Nitro-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrile

Product 1

HCID 224666446-Amino-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrileYield 109.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Added 253 mg 10% palladium on carbon to a round bottom flask under N2 and covered catalyst with 140 ml ethanol. To this added 2.49 g (8.18 mmol) 6-nitro-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrile and 640 μl (20.4 mmol) anhydrous hydrazine. The mixture was heated to reflux for 2 hours 15 minutes and filtered hot through celite. Stripped solvent and dried in vacuo, giving 2.455 g of yellow solid: mass spectrum (electrospray m/e): M+H=275.2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours 15 minutes
  3. filtrationfiltered hot through celite
  4. customStripped solvent and dried in vacuo

Sources & evidence

ORD record
ord-a788b1a06a1b47b0acd6c814358d734f
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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