Phosphorus oxychloride → 2-Amino-3-cyano4-chloroquinoline

HRID 28382Notes

Reaction equation

HRID 28382 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]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:17])=O>[OH-].[Na+]>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([Cl:17])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510455HCID 178510455, compound

Product 1

HCID 114811212-Amino-3-cyano4-chloroquinoline

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 10 g of 2-amino-3-cyano-4-hydroxyquinoline and 15 ml of phosphoryl chloride is heated under stirring at 110° C. The reaction mixture is cooled down, poured onto 100 ml of ice-water and neutralized with 60 ml of 10% sodium hydroxide solution. The resulting yellow precipitate is filtered off, washed with 50 ml of water. After drying 7.5 g of the title compound is obtained, mp.: 210° C.

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled down
  3. filtrationThe resulting yellow precipitate is filtered off
  4. washwashed with 50 ml of water
  5. dry with materialAfter drying 7.5 g of the title compound
  6. customis obtained

Sources & evidence

ORD record
ord-12c450da412f4491aa23fc7ae65f7156
Source dataset
uspto-grants-2008_09
Patent number
US07419977B2

Reaction notes

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