Thionyl Chloride → HCID 20264132, compound

HRID 358441Notes

Reaction equation

HRID 358441 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]([CH2:19][CH3:20])[CH:10]=[C:9]([C:21](O)=[O:22])[C:8]2=[O:24])(=[O:3])[CH3:2].S(Cl)([Cl:27])=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]([CH2:19][CH3:20])[CH:10]=[C:9]([C:21]([Cl:27])=[O:22])[C:8]2=[O:24])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 12873134HCID 12873134, compound

Product 1

HCID 20264132HCID 20264132, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 6,7-diacetoxy-1-ethyl-1,4-dihydro-4-oxoquinoline-3-caroxylic acid (60 mg), thionyl chloride (40 μL), and dimethylformamide (one drop) was heated under reflux for 3 hours in benzene (40 mL), and then the solvent was evaporated. To the residue was added benzene (20 mL). Benzene was evaporated and the residue was vacuum dried to give 6,7-diacetoxy-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carbonyl chloride.

Workup

  1. temperaturewas heated
  2. customthe solvent was evaporated
  3. additionTo the residue was added benzene (20 mL)
  4. customBenzene was evaporated
  5. customdried

Sources & evidence

ORD record
ord-6d4f069b2b0142928320fcdb33bf7e8a
Source dataset
uspto-grants-1984_08
Patent number
US04468394

Reaction notes

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