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

HRID 1759553Notes

Reaction equation

HRID 1759553 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.Cl>[OH-].[Na+]>[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

4

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 2089337-(3-Aminopyrrolidin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 7-(3-acetylamino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (0.88 g) in 10% sodium hydroxide (15 ml) was heated to reflux for 5 hours with stirring. The solution was neutralized with 20% hydrochloric acid to give a precipitate, which was collected, washed successively with water and ethanol, dissolved in 10% acetic acid, and adjusted to pH 7.5-8.0 with 10% aqueous ammonia. There were obtained 0.70 g of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, m.p. 259°-262° C. (decomp.).

Workup

  1. temperatureto reflux for 5 hours
  2. customto give a precipitate, which
  3. customwas collected
  4. washwashed successively with water and ethanol
  5. dissolutiondissolved in 10% acetic acid

Sources & evidence

ORD record
ord-60a408452eb042e3a7dab129c880215f
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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