Ethanol → HCID 22897228, compound

HRID 1017713Notes

Reaction equation

HRID 1017713 reaction equation
[Cl:1]C1C=CC(C=O)=C([N+]([O-])=O)C=1.[C:13]([O:21]CC)(=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[CH2:30](O)[CH3:31]>[Pd]>[CH2:18]([O:17][C:15]([C:14]1[C:13](=[O:21])[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([Cl:1])=[CH:27][CH:26]=2)=[O:16])[CH3:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 796744-Chloro-2-nitrobenzaldehyde

Product 1

HCID 22897228HCID 22897228, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
23 °C

Procedure

A mixture of 4-chloro-2-nitrobenzaldehyde (7-1, 3.00 g, 16.0 mmol, 1 equiv) and 10% palladium on carbon (0.850 g, 0.800 mmol, 0.05 equiv) in ethanol (50 mL) was stirred under a hydrogen balloon for 2 h at 23° C. The catalyst was filtered onto a pad of celite and washed with ethanol (50 mL). The combined filtrate was concentrated to 20 mL, then diethyl malonate (3.92 mL, 25.8 mmol, 1.61 equiv) and piperidine (0.638 mL, 6.45 mmol, 0.403 equiv) were added. The resulting mixture was heated at reflux for 48 h. The mixture was allowed to cool to 23° C., and the precipitate was filtered and washed with cold ethanol (30 mL) to give 6-chloro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (7-2) as a light yellow solid.

Workup

  1. filtrationThe catalyst was filtered onto a pad of celite
  2. washwashed with ethanol (50 mL)
  3. concentrationThe combined filtrate was concentrated to 20 mL
  4. temperatureThe resulting mixture was heated
  5. temperatureat reflux for 48 h
  6. temperatureto cool to 23° C.
  7. filtrationthe precipitate was filtered
  8. washwashed with cold ethanol (30 mL)

Sources & evidence

ORD record
ord-07e0011029c34cffb3bf7063c72ea240
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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