Hydrazine → HCID 22466725, compound

HRID 612248Notes

Reaction equation

HRID 612248 reaction equation
[CH3:1][S: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]([S:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 9321Hydrazine2×HCID 224666284-[(3-Methylsulfanylphenyl)amino]-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 22466725HCID 22466725, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.55 g (13.5 mmol) 4-[(3-methylsulfanylphenyl)amino]-6-nitro-3-quinolinecarbonitrile, 250 ml ethanol, 0.46 g 10% palladium on carbon, and 1.06 ml (33.8 mmol) anhydrous hydrazine was heated to reflux. At 4 hours, added 0.5 equivalents of hydrazine, and at 5 hours, filtered the hot mixture through celite. Stripped the solvent and dried in vacuo, giving 4.068 g brown solid: mass spectrum (electrospray m/e): M+H=307.1.

Workup

  1. temperaturewas heated to reflux
  2. waitat 5 hours
  3. filtrationfiltered the hot mixture through celite
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ad1c3fbf19d44c4089d07693b62d3168
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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