1-Propanol → HCID 20142069, compound

HRID 649115Notes

Reaction equation

HRID 649115 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:12][C:13]3[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=3)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:27](O)CC>S(=O)(=O)(O)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]([CH3:24])[C:19]([O:21][CH2:22][CH2:23][CH3:27])=[O:20])=[CH:25][CH:26]=3)[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10311-PropanolHCID 13079890HCID 13079890, compound

Product 1

HCID 20142069HCID 20142069, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of ethyl 2-[4-(7-chloroquinolin-3-yloxy)phenoxy]propionate (500 mg), concentrated sulphuric acid (2 drops) and n-propanol (50 ml) was heated under reflux with stirring for 72 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and water. The organic layer was separated, dried over magnesium sulphate and evaporated to give n-propyl 2-[4-(7-chloroquinolin-3-yloxy)phenoxy]propionate as a pale brown oil which was characterised by its proton magnetic resonance spectrum (Table 3).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-0d68c370f5ab4e33a445dfe88e61c0fe
Source dataset
uspto-grants-1988_04
Patent number
US04738710

Reaction notes

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