Thionyl Chloride → HCID 20448122, compound

HRID 358450Notes

Reaction equation

HRID 358450 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])[N:11]([CH3:19])[C:10](=[O:20])[C:9]([C:21]([OH:23])=O)=[CH:8]2)(=[O:3])[CH3:2].S(Cl)([Cl:26])=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])[N:11]([CH3:19])[C:10](=[O:20])[C:9]([C:21]([Cl:26])=[O:23])=[CH:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 204481206,7-Diacetoxy-1-methyl-1,2-dihydro-2-oxoquinoline-3-carboxylic acid

Product 1

HCID 20448122HCID 20448122, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

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.

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-742cf43dac6845fea55d7652e32d5573
Source dataset
uspto-grants-1984_08
Patent number
US04468394

Reaction notes

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