Benzyl Chloride → HCID 178469672, compound

HRID 1607298Notes

Reaction equation

HRID 1607298 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:13])[C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]2[OH:19].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O.O>[CH2:26]([O:13][C:10]1[C:11]([F:12])=[C:2]([F:1])[CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]2[OH:19])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178469678HCID 178469678, compound

Product 1

HCID 178469672HCID 178469672, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 6,7-difluoro-4,8-dihydroxy-3-quinolinecarboxylate (300 mg) in dry dimethylformamide (6 ml), was added anhydrous potassium carbonate (308 mg) and then benzyl chloride (145 μl). The mixture was stirred at 55°-65° C. for 11 hours. The reaction mixture was diluted with water (30 ml) and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel (7 g) using acetone/chloroform (1:20) as an eluent to give 113 mg of ethyl 8-benzyloxy-6,7-difluoro-4-hydroxy-3-quinolinecarboxylate, mp 200°-201° C.; MS m/z 359 (M+), after recrystallization from methanol.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel (7 g)

Sources & evidence

ORD record
ord-aac232b6b4db448f9b03767bea92fe33
Source dataset
uspto-grants-1989_09
Patent number
US04864023

Reaction notes

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