Hydrochloric Acid → HCID 17975821, compound

HRID 2108884Notes

Reaction equation

HRID 2108884 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.Cl.C(OCC)C.C([O-])([O-])=O.[K+].[K+]>O.CN1C(=O)CCC1>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:12][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 178516426HCID 178516426, compound

Product 1

HCID 17975821HCID 17975821, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

7-Chloro4-quinolinol (2 g, 11.1 mmol), Li2CO3 (1.7 g, 22.3 mmol) and NMP (16 mL) were charged in a 100 ml round-bottomed flask equipped with a magnetic stirrer. 1,5-Dibromopentane (13.5 g, 55.7 mmol) was added and the reaction mixture was stirred for 1 h at 90° C. The reaction mixture was poured in 100 mL of H2O, extracted with EtOAc (300 mL). The organic layer was washed with water (30 mL), brine (2×30 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. HCl 1M in diethyl ether (15 mL, 15 mmol) was added and the bis-alkylated product was precipitated and filtered. The precipitate was dissolved in water with K2CO3 (1.5 g, 11.1 mmol), extracted with EtOAc (300 mL). The organic layer was washed with brine (2×20 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 95:5) to give after evaporation 4-(5-bromopentyloxy)-7-chloroquinoline 33 (0.45 g, 12% yield) as a white solid.

Workup

  1. customequipped with a magnetic stirrer
  2. extractionextracted with EtOAc (300 mL)
  3. washThe organic layer was washed with water (30 mL), brine (2×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated at 30° C. to dryness
  7. customthe bis-alkylated product was precipitated
  8. filtrationfiltered
  9. extractionextracted with EtOAc (300 mL)
  10. washThe organic layer was washed with brine (2×20 mL)
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customevaporated at 30° C. to dryness
  14. customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 95:5)
  15. customto give

Sources & evidence

ORD record
ord-96a1ca16f4864a0a8d3e9b0c9c888c45
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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