Phosphorus oxychloride → HCID 20142081, compound

HRID 649117Notes

Reaction equation

HRID 649117 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:12][C:13]3[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19]([NH2:21])=O)=[CH:15][CH:14]=3)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:12][C:13]3[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:22])[C:19]#[N:21])=[CH:23][CH:24]=3)[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 20142073HCID 20142073, compound

Product 1

HCID 20142081HCID 20142081, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[4-(7-Chloroquinolin-3-yloxy)phenoxy]propionamide (see Example 23) (1.2 g) was added slowly with stirring to phosphorus oxychloride (10 ml) at 20° C. The mixture was heated briefly to the boiling point then poured on to water and neutralized carefully with aqueous sodium bicarbonate solution. Extraction with ethyl acetate gave, after drying and evaporation, the crude product as a pale yellow oil. Purification by chromatography on silica gel gave 2-[4-(7-chloroquinolin-3-yloxy)phenoxy]propionitrile, characterised by its proton magnetic resonance spectrum (Table 3).

Workup

  1. temperatureThe mixture was heated briefly to the boiling point
  2. extractionExtraction with ethyl acetate
  3. customgave
  4. customafter drying
  5. customevaporation
  6. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-ca5d741527734ef1b5c0ea44036cf7f3
Source dataset
uspto-grants-1988_04
Patent number
US04738710

Reaction notes

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