Hydrochloric Acid → HCID 14050840, compound

HRID 2232089Notes

Reaction equation

HRID 2232089 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:16][CH:15]([Cl:17])[CH:14]([CH2:18][NH:19]C(=O)C)[CH2:13]1)[N:8]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH:7]=[C:6]([C:28]([OH:30])=[O:29])[C:5]2=[O:31].Cl.C(=O)([O-])O.[Na+]>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:16][CH:15]([Cl:17])[CH:14]([CH2:18][NH2:19])[CH2:13]1)[N:8]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH:7]=[C:6]([C:28]([OH:30])=[O:29])[C:5]2=[O:31]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14050839HCID 14050839, compound

Product 1

HCID 14050840HCID 14050840, compoundYield 89.5%

Procedure

To 6-fluoro-1-(2-thienyl)-7-(3-acetylaminomethyl-4-chloro-1-pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.43 g) is added 20% hydrochloric acid (8 ml), and the mixture is refluxed for 5 hours. After cooling, the mixture is neutralized with saturated aqueous sodium hydrogen carbonate, the precipitated crystals are separated by filtration and dried. The product is converted into its hydrochloride by treating it with a hydrochloric acid-saturated ethanol, and the resulting crude crystals are recrystallized from ethanol-ether to give 6-fluoro-1-(2-thienyl)-7-(3-aminomethyl-4-chloro-1-pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.35 g).

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. customthe precipitated crystals are separated by filtration
  4. customdried
  5. additionby treating it with a hydrochloric acid-saturated ethanol
  6. customthe resulting crude crystals are recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-4697f781a88b410ebef1ba924dcb3b39
Source dataset
uspto-grants-1988_11
Patent number
US04786649

Reaction notes

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