Sodium Hydroxide → 2-Amino-3-cyano-4-chloro-6-(2,6-dimethylmorpholin-4-yl)quinoline

HRID 2195689Notes

Reaction equation

HRID 2195689 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][CH:19]([CH3:21])[O:18][CH:17]([CH3:22])[CH2:16]3)[CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:25])=O.[OH-].[Na+]>>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([Cl:25])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:15]3[CH2:20][CH:19]([CH3:21])[O:18][CH:17]([CH3:22])[CH2:16]3)[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178429869HCID 178429869, compound

Product 1

HCID 670235572-Amino-3-cyano-4-chloro-6-(2,6-dimethylmorpholin-4-yl)quinoline

Conditions

Temperature
120 °C

Procedure

The mixture of 1.7 g of 2-amino-3-cyano-4-hydroxy-6-(2,6-dimethylmorpholin-4-yl)quinoline 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% sodium hydroxide solution, and the precipitated material is filtered off. After drying 1.5 g of the title compound is obtained (MH+: 317).

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 (MH+: 317)

Sources & evidence

ORD record
ord-ec036296324d4cad8e126ace605ffcbc
Source dataset
uspto-grants-2012_12
Patent number
US08338411B2

Reaction notes

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