Phosphorus oxychloride → 4-Chloro-6,7-dimethoxyquinoline

HRID 491666Notes

Reaction equation

HRID 491666 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2O.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486804HCID 178486804, compound

Product 1

HCID 4596104-Chloro-6,7-dimethoxyquinoline

Conditions

Temperature
85 °C

Procedure

6,7-Dimethoxy-4-hydroxyquinoline (Step A, 7.8 g) was dissolved in POCl3 (45 mL) and heated at 85° C. for 3 h. The mixture was cooled down to RT, POCl3 was evaporated and the resulting oil was quenched by adding ice at 0° C. The aqueous phase was basified to pH 8 and a solid precipitated. The solid was filtered and dried under vacuum to give 4-chloro-6,7-dimethoxyquinoline.

Workup

  1. temperatureThe mixture was cooled down to RT
  2. customPOCl3 was evaporated
  3. customthe resulting oil was quenched
  4. additionby adding ice at 0° C
  5. customa solid precipitated
  6. filtrationThe solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-145f3eb5518541a587a7e57c1039a431
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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