Hydrazine → 6-Amino-4-(3-dimethylaminophenylamino)quinoline-3-carbonitrile

HRID 1935179Notes

Reaction equation

HRID 1935179 reaction equation
[CH3:1][N:2]([CH3:25])[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>CCO.[Pd]>[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]([N:2]([CH3:25])[CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 224666434-(3-Dimethylaminophenylamino)-6-nitroquinoline-3-carbonitrile

Product 1

HCID 224667536-Amino-4-(3-dimethylaminophenylamino)quinoline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (15.0 mmol) of 4-(3-dimethylaminophenylamino)-6-nitro-quinoline-3-carbonitrile, 1.20 g (37.5 mmol) of anhyd hydrazine and 0.5 g of 10% Pd/C in 250 mL of EtOH was refluxed under N2 for 1.3 hr. The reaction was filtered through Celite, the Celite was washed with EtOH and the filtrate and washes were combined. Solvent evaporation and drying in vacuo (50° C.) gave 6-amino-4-(3-dimethylaminophenylamino)quinoline-3-carbonitrile as a red brown solid: mass spectrum (electrospray, m/e): 303.9.

Workup

  1. temperaturewas refluxed under N2 for 1.3 hr
  2. filtrationThe reaction was filtered through Celite
  3. washthe Celite was washed with EtOH
  4. customSolvent evaporation
  5. customdrying in vacuo (50° C.)

Sources & evidence

ORD record
ord-3cc18901189a41bc87e3638a9ee43e81
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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