Reaktion #445632

ord-742cf43dac6845fea55d7652e32d5573

Reaktionsgleichung

CC(=O)Oc1cc2cc(C(=O)O)c(=O)n(C)c2cc1OC(C)=O
6,7-diacetoxy-1-methyl-1,2-dihydro-2-oxoquinoline-3-carboxylic acid
O=S(Cl)Cl
thionyl chloride
→
CC(=O)Oc1cc2cc(C(=O)Cl)c(=O)n(C)c2cc1OC(C)=O
6,7-diacetoxy-1-methyl-1,2-dihydro-2-oxoquinoline-3-carbonyl chloride

Edukte

CC(=O)Oc1cc2cc(C(=O)O)c(=O)n(C)c2cc1OC(C)=O
6,7-diacetoxy-1-methyl-1,2-dihydro-2-oxoquinoline-3-carboxylic acid
O=S(Cl)Cl
thionyl chloride

Reagenzien

CN(C)C=O
dimethylformamide

Lösungsmittel

c1ccccc1
benzene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas heated
  2. 2
    workup.DISTILLATIONthe solvent was distilled off
  3. 3
    workup.ADDITIONBenzene (30 mL) was added to the residue
  4. 4
    workup.DISTILLATIONthe benzene was distilled off again
  5. 5
    Sonstigedrying

Vorschrift

A mixture of 6,7-diacetoxy-1-methyl-1,2-dihydro-2-oxoquinoline-3-carboxylic acid (60 mg), thionyl chloride (40 μL), and dimethylformamide (one drop) was heated under reflux for 2 hours in 40 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-methyl-1,2-dihydro-2-oxoquinoline-3-carbonyl chloride.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04468394uspto-grants-1984_08