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

HRID 902171Notes

Reaction equation

HRID 902171 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-hydroxyquinolin 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-2c156f3de827497c90f80c2f381f9576
Source dataset
uspto-grants-2008_04
Patent number
US07365089B2

Reaction notes

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