HCID 66636954, compound → 7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde

HRID 469238Notes

Reaction equation

HRID 469238 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:25])[C:13]([CH2:23][OH:24])=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[O-2].[O-2].[Mn+4].ClCCl>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:25])[C:13]([CH:23]=[O:24])=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 66636954HCID 66636954, compound

Product 1

HCID 866330517-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehydeYield 94.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 100 ml dichloromethane solution of 13.8 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(hydroxymethyl)quinolin-4(1H)-one was added 67.0 g of manganese dioxide at room temperature, followed by overnight stirring. After completion of the reaction and subsequent filtration using celite, the filtrate was evaporated under a reduced pressure. By crystallizing the resulting solid from ethyl acetate, 13.0 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde was obtained.

Workup

  1. customAfter completion of the reaction and subsequent filtration
  2. customthe filtrate was evaporated under a reduced pressure
  3. customBy crystallizing the resulting solid from ethyl acetate

Sources & evidence

ORD record
ord-db61c75c291847199b52995858b3510f
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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