1-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinoline → 1-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-3-formyl-1,4-dihydro-4oxoquinoline

HRID 1073761Notes

Reaction equation

HRID 1073761 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:24])[C:10]([F:23])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH:20]=[O:21])[CH:16]([CH3:22])[CH2:15]4)[CH:12]=3)[C:7](=[O:25])[CH:6]([CH:26]=[O:27])[CH2:5]2)[CH2:3][CH2:2]1>CO.[O-2].[O-2].[Mn+4]>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:24])[C:10]([F:23])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH:20]=[O:21])[CH:16]([CH3:22])[CH2:15]4)[CH:12]=3)[C:7](=[O:25])[C:6]([CH:26]=[O:27])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 157127251-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinoline

Product 1

HCID 157127271-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-3-formyl-1,4-dihydro-4oxoquinolineYield 98%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

1-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl-1,2,3,4-tetrahydroquinoline (4.0 g) is dissolved in methanol (150 ml) and thereto is added manganese dioxide (9.3 g), and the mixture is stirred at room temperature for 2 hours. After removing manganese dioxide by filtration with celite, the filtrate is concentrated, and the resulting residue is recrystallized from ethanol to give 1-cyclopropyl-6-fluoro-7-(4-formyl-3 -methyl-1-piperazinyl)-5-methyl-3-formyl-1,4-dihydro-4oxoquinoline (3.9 g), as pale yellow powdery crystals, m.p. 258°-260° C.

Workup

  1. customAfter removing manganese dioxide
  2. filtrationby filtration with celite
  3. concentrationthe filtrate is concentrated
  4. customthe resulting residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-5d328b6897474bb191e0dc07d4a43907
Source dataset
uspto-grants-1990_11
Patent number
US04971970

Reaction notes

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