Water → Methyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

HRID 326650Notes

Reaction equation

HRID 326650 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[CH:5]=[C:6]([C:13]([O:15][CH3:16])=[O:14])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O>[CH2:24]([O:17][C:4]1[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[N:7]=[C:6]([C:13]([O:15][CH3:16])=[O:14])[CH:5]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14743007Methyl 5,7-dichloro-4-hydroxyquinoline-2-carboxylate

Product 1

HCID 19735155Methyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of methyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate (3 g) in dry dimethyl-formamide (20 ml) was added potassium carbonate (6.1 g) followed by benzyl bromide (1.44 ml) and the mixture stirred at room temperature for 16 hours. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (3×100 ml), the organic layers were combined and washed with water (2×100 ml), 1M hydrochloric acid (1×100 ml), brine (2×100 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure and the crude product purified by column chromatography to give methyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (2.8 g). δ (360 MHz, DMSO-d6) 3.95 (3H, s, OCH3), 5.48 (2H, s, CH2), 7.35 (1H, d, p-ArH), 7.38 (2H, t, m-ArH), 7.46 (2H, d, o-ArH), 7.59 (1H, s, 3-H), 7.83 (1H, d, 6-H) and 8.11 (1H, d, 8-H).

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washwashed with water (2×100 ml), 1M hydrochloric acid (1×100 ml), brine (2×100 ml)
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product purified by column chromatography

Sources & evidence

ORD record
ord-24557c60eded4680bbf71a1518d52b12
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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