Water → HCID 178487709, compound

HRID 1675428Notes

Reaction equation

HRID 1675428 reaction equation
[CH:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([CH3:3])[CH3:2].Cl[C:10]1[CH:19]=[C:18]([O:20]CC2C=CC(OC)=CC=2)[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([O:30][CH3:31])=[CH:15][CH:16]=2)[N:11]=1.O>CN1CCCC1=O>[OH:20][C:18]1[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([O:30][CH3:31])=[CH:15][CH:16]=2)[N:11]=[C:10]([N:6]2[CH:7]=[CH:8][C:4]([CH:1]([CH3:3])[CH3:2])=[N:5]2)[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 566051592-Chloro-8-methyl-7-methoxy-4-(4-methoxy-benzyloxy)-quinolineHCID 178439403HCID 178439403, compound

Product 1

HCID 178487709HCID 178487709, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of compound 86b (350 mg, 1 eq.) and compound 46b (480 mg, 6 eq.) in N-methylpyrrolidone (5 mL) was heated at 200° C. for 30 min. After the reaction mixture was cooled to room temperature, water was added. The mixture was extracted with EtOAc, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (EtOAc/DCM). Recrystallisation in diethylether gave compound 88b as a white solid in 49% yield.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by chromatography on silica gel (EtOAc/DCM)
  6. customRecrystallisation in diethylether

Sources & evidence

ORD record
ord-7643627824114f599057a7f2466ec571
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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