Hydrochloric Acid → HCID 13565849, compound

HRID 1589563Notes

Reaction equation

HRID 1589563 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](Cl)[N:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[OH-].[K+].[CH2:21]([SH:23])[CH3:22].Cl>CN(C)C=O.C(O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([S:23][CH2:21][CH3:22])[N:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 14797Potassium HydroxideHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 13565849HCID 13565849, compoundYield 182.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 0.54 g (2 mmol) 1-ethyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid in 10 ml N,N-dimethyl formamide was stirred at 60° C. and treated all at once with a solution of 0.56 g potassium hydroxide (10 mmol) and 1 ml (0.85 mmol) ethanethiol in 5 ml absolute ethanol. After 15 minutes the mixture was poured into 40 mmol 0.4 N hydrochloric acid containing ice. The precipitate was filtered, washed with ethanol and ether to afford 0.46 g of the title compound. A sample for analysis was crystallized from acetic acid, mp 219°-221° C.

Workup

  1. additioncontaining ice
  2. filtrationThe precipitate was filtered
  3. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-203da94061104feea3cc959c5211d9f4
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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