Potassium Hydroxide → HCID 12899691, compound

HRID 1649444Notes

Reaction equation

HRID 1649444 reaction equation
[N:1]1([C:7]2[C:18]3=[C:19]4[N:14]([CH2:15][CH2:16][CH2:17]3)[CH:13]=[C:12]([C:20]([OH:22])=[O:21])[C:11](=[O:23])[C:10]4=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[K+].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>O>[CH3:26][S:27]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:18]3=[C:19]4[N:14]([CH2:15][CH2:16][CH2:17]3)[CH:13]=[C:12]([C:20]([OH:22])=[O:21])[C:11](=[O:23])[C:10]4=[CH:9][CH:8]=2)[CH2:2][CH2:3]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 12899683HCID 12899683, compound

Product 1

HCID 12899691HCID 12899691, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.0 g of 8-(1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid was dissolved in 20 ml of water having dissolved therein 0.8 g of potassium hydroxide and 0.8 g of methanesulfonyl chloride was added dropwise to the solution. The resulting mixture was allowed to stand overnight at the same temperature as above while stirring. The crystals precipitated were separated by filtration and washed with water. The crystals thus-treated were dissolved in 1 N aqueous sodium hydroxide solution and the solution was treated with activated carbon and rendered neutral with a 10% aqueous hydrochloric acid solution to precipitate crystals, which were separated by filtration and washed with water. Recrystallization of the crystals thus-obtained from dimethylformamide gave 1.0 g of 8-(4-methanesulfonyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as white needles having a melting point of not lower than 300° C.

Workup

  1. dissolutiondissolved
  2. customThe crystals precipitated
  3. customwere separated by filtration
  4. washwashed with water
  5. additionThe crystals thus-treated
  6. dissolutionwere dissolved in 1 N aqueous sodium hydroxide solution
  7. additionthe solution was treated with activated carbon
  8. customto precipitate crystals, which
  9. customwere separated by filtration
  10. washwashed with water
  11. customRecrystallization of the crystals
  12. customthus-obtained from dimethylformamide

Sources & evidence

ORD record
ord-a99edd9d80fa421aae368cd5bcce00dd
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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