Sodium Hydroxide → 2-Amino-3-cyano-4-chloro-6-dimethylaminoquinoline

HRID 1715811Notes

Reaction equation

HRID 1715811 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]([CH3:17])[CH3:16])[CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:20])=O.[OH-].[Na+]>>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([Cl:20])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:15]([CH3:17])[CH3:16])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178482613HCID 178482613, compound

Product 1

HCID 668503782-Amino-3-cyano-4-chloro-6-dimethylaminoquinoline

Conditions

Temperature
120 °C

Procedure

The mixture of 1.7 g of 2-amino-3-cyano-4-hydroxy-6-dimethylaminoquinoline and 3.4 mL of phosphoryl chloride is stirred at 120° C. for 4 hours. The cooled reaction mixture is poured onto 30 g of ice, the pH of the mixture is adjusted to 8 with 10% NaOH solution and the precipitated material is filtered off. After drying 1.5 g of the title compound is obtained, m.p.: 285° C.

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe precipitated material is filtered off
  3. dry with materialAfter drying 1.5 g of the title compound
  4. customis obtained

Sources & evidence

ORD record
ord-78cef072a6cd4ae0acedfa5384acac02
Source dataset
uspto-grants-2010_09
Patent number
US07799922B2

Reaction notes

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