Acetic Acid → HCID 13044292, compound

HRID 434684Notes

Reaction equation

HRID 434684 reaction equation
[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[N:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1.[C:27](O)(=[O:29])[CH3:28]>S(=O)(=O)(O)O.ClCCl>[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[N:20]1[CH2:21][CH2:22][CH:23]([O:26][C:27](=[O:29])[CH3:28])[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 4410Nadifloxacin

Product 1

HCID 13044292HCID 13044292, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 25 ml flask were placed 0.43 g of 9-fluoro-8-(4-hydroxy-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 0.2 g of acetic acid and 5 ml of dichloromethane and the mixture was refluxed after adding 5 drops of concentrated sulfuric acid. During the reaction oily substance appeared on the bottom of the flask. After 5 hours the reaction was stopped, dichloromethane was removed and water was added to the product followed by filtration. Crystals thus obtained were washed with methanol to give 150 mg of 9-fluoro-8-(4-acetoxy-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 250°-253° C., pale yellow rhombic crystals.

Workup

  1. customIn a 25 ml flask were placed
  2. customdichloromethane was removed
  3. additionwater was added to the product
  4. filtrationfollowed by filtration
  5. customCrystals thus obtained
  6. washwere washed with methanol

Sources & evidence

ORD record
ord-a570b368a10c4d128dd032c00696df2e
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

Loading…