Dimethyl Sulfoxide → HCID 19848074, compound

HRID 2351024Notes

Reaction equation

HRID 2351024 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1Cl)[N:14]([NH:19][CH3:20])[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[C:11]2=[O:24].B(F)(F)O.[OH-].[Na+].[CH3:31]S(C)=O>>[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)[N:14]([NH:19][CH2:20][CH3:31])[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[C:11]2=[O:24]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 4837PiperazineHCID 14798Sodium HydroxideHCID 139635DifluorohydroxyboraneHCID 30212917-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 19848074HCID 19848074, compoundYield 82%

Conditions

Temperature
110 °C

Procedure

A mixture of 5.18 g of piperazine and 6.37 g of an anhydride of 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid and difluoroboric acid formed with 32 ml of dimethyl sulfoxide is stirred at 110° C. for 3 hours. To the reaction mixture 51 ml of a 6 weight/vol % aqueous sodium hydroxide solution are added and the aqueous reaction mixture is stirred under slight boiling for 2 hours. The reaction mixture is filtered, the filtrate is evaporated in vacuo to two-thirds of its volume and the pH of the solution is adjusted to 6.5-7 by adding acetic acid. The reaction mixture is allowed to crystallize in a refrigerator overnight. Next morning the precipitated crystals are filtered, washed twice with 10 ml of water each and with 5 ml of methanol. Thus 5.3 g of 6-fluoro-1-ethylamino-7-piperazino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid are obtained. Yield: 82%. Mp.: 289°-291° C. (decomposition; from dimethyl formamide).

Workup

  1. stirringthe aqueous reaction mixture is stirred under slight boiling for 2 hours
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated in vacuo to two-thirds of its volume
  4. additionby adding acetic acid
  5. customto crystallize in a refrigerator overnight
  6. filtrationNext morning the precipitated crystals are filtered
  7. washwashed twice with 10 ml of water each and with 5 ml of methanol

Sources & evidence

ORD record
ord-cde0a3503f9a4f31b1b8bb8c20ab353f
Source dataset
uspto-grants-1989_10
Patent number
US04871849

Reaction notes

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