Pyrrolidine → 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pyrrolidinyl)-1,8-naphthyridine-3-carboxylic acid

HRID 1759560Notes

Reaction equation

HRID 1759560 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(#N)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 130411391-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pyrrolidinyl)-1,8-naphthyridine-3-carboxylic acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (1.0 g), pyrrolidine (1.31 g), and acetonitrile (80 ml) was heated under reflux for 2 hours. The reaction mixture was concentrated to dryness under reduced pressure. The residue was mixed with 5% hydrochloric acid (25 ml) and the mixture was heated on a steam-bath for several minutes and then cooled. The resulting precipitate was collected, washed with water, and recrystallized from chloroform-ethyl acetate to give 1.0 g of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-pyrrolidinyl)-1,8-naphthyridine-3-carboxylic acid, m.p. 299°-300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. additionThe residue was mixed with 5% hydrochloric acid (25 ml)
  5. temperaturethe mixture was heated on a steam-bath for several minutes
  6. temperaturecooled
  7. customThe resulting precipitate was collected
  8. washwashed with water
  9. customrecrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-7e2af5d0297d4b40a7539b6f55f34096
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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