Hydrochloric Acid → 7-(3-Aminopyrrolidin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid--hydrogen chloride (1/1)

HRID 1759552Notes

Reaction equation

HRID 1759552 reaction equation
C([NH:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:25])[C:15]([C:22]([OH:24])=[O:23])=[CH:16][N:17]3[CH2:20][CH3:21])=[CH:12][C:11]=2[F:26])[CH2:6]1)(=O)C.[ClH:27]>>[ClH:27].[NH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:25])[C:15]([C:22]([OH:24])=[O:23])=[CH:16][N:17]3[CH2:20][CH3:21])=[CH:12][C:11]=2[F:26])[CH2:6]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 130411377-[3-(Acetylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 30614697-(3-Aminopyrrolidin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid--hydrogen chloride (1/1)

Procedure

A mixture of 7-(3-acetylamino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (1.81 g) in 20% hydrochloric acid (20 ml) was heated under reflux for 3 hours with stirring. The mixture was concentrated to dryness under reduced pressure and then ethanol was added to the residue. After cooling the mixture, the resulting solid was collected and recrystallized from ethanol-water to yield 1.64 g of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride (Compound 1), m.p. 285°-290° C. (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe mixture was concentrated to dryness under reduced pressure
  4. additionethanol was added to the residue
  5. temperatureAfter cooling the mixture
  6. customthe resulting solid was collected
  7. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-8a131d4acf5448daaa9fa1f1ddb09bd5
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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