Ethyl 7-[2(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate → 1-Ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 978512Notes

Reaction equation

HRID 978512 reaction equation
C(NCC1SC=C([C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:23]([O:25]CC)=[O:24])=[CH:17][N:18]3[CH2:21][CH3:22])=[CH:13][C:12]=2[F:29])N=1)(=O)C>Cl>[CH2:21]([N:18]1[C:19]2[C:14](=[CH:13][C:12]([F:29])=[CH:11][CH:20]=2)[C:15](=[O:28])[C:16]([C:23]([OH:25])=[O:24])=[CH:17]1)[CH3:22]

Participants

3

Reactant 1

HCID 13772764Ethyl 7-[2(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 107048941-Ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 0.32 g (0.76 mmol) ethyl 7-[2-(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 3 ml 6N hydrochloric acid was stirred at reflux three hours. The mixture was evaporated to dryness and the resulting solid was suspended in 5 ml water and dissolved by addition of 1N sodium hydroxide to pH 11. After filtration the product was precipitated by addition of 1N hydrochloric acid to pH 6.2, filtered, washed with water and dried to afford 0.22 g 7-[2-aminomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 249°-254° C. (dec).

Workup

  1. temperatureat reflux three hours
  2. customThe mixture was evaporated to dryness
  3. dissolutiondissolved by addition of 1N sodium hydroxide to pH 11
  4. filtrationAfter filtration the product
  5. customwas precipitated by addition of 1N hydrochloric acid to pH 6.2
  6. filtrationfiltered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-eabe7516c6924919ac382ec0ab62b1aa
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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