Hydrazine hydrate (1:1) → HCID 9887640, compound

HRID 1489171Notes

Reaction equation

HRID 1489171 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:39])=[C:11]([N:16]4[CH2:20][CH2:19][C@@:18]([CH2:23][N:24](CC5C=CC=CC=5)CC5C=CC=CC=5)([CH2:21][F:22])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:40])[C:6]([C:41]([OH:43])=[O:42])=[CH:5]2)[CH2:3][CH2:2]1.O.NN>C(O)C.[OH-].[Na+].[C].[Pd]>[NH2:24][CH2:23][C@@:18]1([CH2:21][F:22])[CH2:19][CH2:20][N:16]([C:11]2[C:12]([O:14][CH3:15])=[C:13]3[C:8]([C:7](=[O:40])[C:6]([C:41]([OH:43])=[O:42])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:39])[CH2:17]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54070758HCID 54070758, compound

Product 1

HCID 9887640HCID 9887640, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(S)-1-Cyclopropyl-7-(3-(N,N-dibenzylaminomethyl)-3-fluoromethylpyrrolidin-1-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (19.58 g) was dissolved in ethanol (300 ml), and 10% palladium-carbon (3.9 g) and hydrazine hydrate (5.0 g) were added. The mixture was refluxed with stirring for 4 hours. The precipitated crystals were dissolved in a 2N aqueous solution of sodium hydroxide. The mixture was filtrated to remove the catalyst. After concentration, water (100 ml) was added and the pH of the solution was adjusted to 7 with dilute hydrochloric acid. The precipitated crystals were collected by filtration to give the object compound, melting point 188°-190° C.

Workup

  1. temperatureThe mixture was refluxed
  2. filtrationThe mixture was filtrated
  3. customto remove the catalyst
  4. concentrationAfter concentration, water (100 ml)
  5. additionwas added
  6. filtrationThe precipitated crystals were collected by filtration
  7. customto give the object compound, melting point 188°-190° C.

Sources & evidence

ORD record
ord-141b09b22ab043d8a42d5e1219cbb46c
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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