Hydrazine → HCID 22466720, compound

HRID 1935180Notes

Reaction equation

HRID 1935180 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1.NN>[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:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:25])[CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22466751HCID 22466751, compound

Product 1

HCID 22466720HCID 22466720, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Prepared from 4-(4-dimethylaminophenylamino)-6-nitroquinoline-3-carbonitrile (5.00 g), 1.20 g of anhyd hydrazine and 0.500 g of 10% Pd/C in the same manner as EXAMPLE 388 155179. After washing first with MeOH (discarded), the product was eluted with DMF. The latter solvent was collected separately, evaporated and the residue was dried in vacuo (50° C.). The yield of 6-amino-4-(4-dimethylaminophenylamino)quinoline-3-carbonitrile was 4.00 g as a yellow solid: mass spectrum (electrospray, m/e): M+H 303.9.

Workup

  1. washAfter washing first with MeOH (discarded)
  2. washthe product was eluted with DMF
  3. customThe latter solvent was collected separately
  4. customevaporated
  5. customthe residue was dried in vacuo (50° C.)

Sources & evidence

ORD record
ord-22cb55e3847c4bfebb06a72d6e534944
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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