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

HRID 2233275Notes

Reaction equation

HRID 2233275 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-ac4da97542b042a68c9ea58f7e2ef134
Source dataset
uspto-grants-2010_05
Patent number
US07709489B2

Reaction notes

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