HCID 86696916, compound → 7-(3-Chloropropoxy)-6-methoxyquinolin-4-OL

HRID 68533Notes

Reaction equation

HRID 68533 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14](=[O:20])/[CH:15]=[CH:16]/N(C)C)=[C:8]([N+:21]([O-])=O)[CH:7]=1>C(O)(=O)C.[Fe]>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:9]([C:14](=[O:20])[CH:15]=[CH:16][NH:21]2)=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 1

HCID 86696916HCID 86696916, compound2×

Product 1

HCID 717440127-(3-Chloropropoxy)-6-methoxyquinolin-4-OLYield 67.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

Intermediate IV (150 g, 0.44 mol) was added to glacial acetic acid (8v/w, 1200 mL). The mixture was warmed up to 40° C. After Intermediate IV was dissolved completely, iron powder (123.1 g, 2.20 mol) was slowly added in batch. The mixture was warmed up to 80° C. and reacted under mechanical stirring for 2 h. After completion of the reaction, the reaction solution was filtered by suction when it is still hot. The filtrate was collected. After cooling the filtrate, a great deal of solid separated out and was filtered by suction to produce a lutescens solid. The filtered cake was dissolved in glacial acetic acid. The mixture was stirred at 80° C. for about 30 min, and was filtered by suction again when it is still hot. The filtrate was collected. After cooling the filtrate, a solid separated out and was filtered by suction to produce a lutescens solid. The solids were combined, and washed with water several times until the filtrate became neutral. The filtered cake was dried to produce a pale yellow solid (79 g) in a yield of 65%.

Workup

  1. temperatureThe mixture was warmed up to 80° C.
  2. customreacted
  3. customAfter completion of the reaction
  4. filtrationthe reaction solution was filtered by suction when it
  5. customThe filtrate was collected
  6. temperatureAfter cooling the filtrate
  7. customa great deal of solid separated out
  8. filtrationwas filtered by suction
  9. customto produce a lutescens solid
  10. stirringThe mixture was stirred at 80° C. for about 30 min
  11. filtrationwas filtered by suction again when it
  12. customThe filtrate was collected
  13. temperatureAfter cooling the filtrate
  14. customa solid separated out
  15. filtrationwas filtered by suction
  16. customto produce a lutescens solid
  17. washwashed with water several times until the filtrate
  18. customThe filtered cake was dried

Sources & evidence

ORD record
ord-ce660921652a4a569557cd90a8f6ce41
Source dataset
uspto-grants-2014_09
Patent number
US08822465B2

Reaction notes

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