Thionyl Chloride → Methyl 7-(benzyloxy)-4-chloro-6-quinolinecarboxylate

HRID 387916Notes

Reaction equation

HRID 387916 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=O)[CH:18]=[CH:19][NH:20]2)=[CH:15][C:14]=1[C:24]([O:26][CH3:27])=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O>[CH2:5]([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]([Cl:3])=[CH:18][CH:19]=[N:20]2)=[CH:15][C:14]=1[C:24]([O:26][CH3:27])=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22936245Methyl 7-(benzyloxy)-4-oxo-1,4-dihydro-6-quinolinecarboxylate

Product 1

HCID 22936661Methyl 7-(benzyloxy)-4-chloro-6-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After adding thionyl chloride (70 ml) and a catalytic amount of dimethylformamide to methyl 7-(benzyloxy)-4-oxo-1,4-dihydro-6-quinolinecarboxylate (7.19 g, 23.2 mmol), the mixture was heated to reflux for 3 hours while stirring. The reaction solution was concentrated under reduced pressure, a 2N sodium hydroxide solution was gradually added for neutralization, extraction was performed with ethyl acetate, and the organic layer was washed with water and saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off, diethyl ether was added for crystallization, and the crystals were filtered out and blow-dried to obtain the title compound (4.067 g, 12.4 mmol) as light brown crystals.

Workup

  1. temperatureto reflux for 3 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additiona 2N sodium hydroxide solution was gradually added for neutralization, extraction
  4. washthe organic layer was washed with water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. additiondiethyl ether was added for crystallization
  8. filtrationthe crystals were filtered out and
  9. customblow-dried

Sources & evidence

ORD record
ord-64e92a53bf00491fa05cac060a89fc8e
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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