Thionyl Chloride → HCID 20448116, compound

HRID 358449Notes

Reaction equation

HRID 358449 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[NH:11][C:10](=[O:19])[C:9]([C:20]([OH:22])=O)=[CH:8]2)(=[O:3])[CH3:2].S(Cl)([Cl:25])=O>CN(C)C=O.C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[NH:11][C:10](=[O:19])[C:9]([C:20]([Cl:25])=[O:22])=[CH:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20448121HCID 20448121, compound

Product 1

HCID 20448116HCID 20448116, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 6,7-diacetoxy-1,2-dihydro-2-oxoquinoline-3-carboxylic acid (100 mg), thionyl chloride (70 μL), and dimethylformamide (one drop) was heated under reflux for 4.5 hours in 50 mL of benzene, and the solvent was distilled off. Benzene (30 mL) was added to the residue and the benzene was distilled off again, followed by vacuum drying, to yield 6,7-diacetoxy-1,2-dihydro-2-oxoquinoline-3-carbonyl chloride.

Workup

  1. temperaturewas heated
  2. distillationthe solvent was distilled off
  3. additionBenzene (30 mL) was added to the residue
  4. distillationthe benzene was distilled off again
  5. customdrying

Sources & evidence

ORD record
ord-4ebc0e9f6fc4498cab6986ace868f293
Source dataset
uspto-grants-1984_08
Patent number
US04468394

Reaction notes

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