Sodium Hydroxide → 2-Amino-3-cyano-4-chloro-6-(4-acetylpiperazin-1-yl)quinoline

HRID 2195695Notes

Reaction equation

HRID 2195695 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10](O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]3)[CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:26])=O.[OH-].[Na+]>C(#N)C>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([Cl:26])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178473878HCID 178473878, compound

Product 1

HCID 670236312-Amino-3-cyano-4-chloro-6-(4-acetylpiperazin-1-yl)quinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 1.7 g 2-amino-3-cyano-4-hydroxy-6-(4-acetylpiperazin-1-yl)quinoline, 50 ml acetonitrile and 3.4 ml phosphoryl chloride is heated at reflux temperature for 4 hours. The cooled reaction mixture is poured onto 30 g ice, the pH of the mixture is set to 8 with 10% sodium hydroxide solution and the resulting precipitate is filtered off. After drying 1.5 g of the title compound is obtained (MH+: 330).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 hours
  3. customThe cooled reaction mixture
  4. filtrationthe resulting precipitate is filtered off
  5. dry with materialAfter drying 1.5 g of the title compound
  6. customis obtained (MH+: 330)

Sources & evidence

ORD record
ord-ab6b82694678450b85ddf3844f42e428
Source dataset
uspto-grants-2012_12
Patent number
US08338411B2

Reaction notes

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