Diethyl Malonate → HCID 22897229, compound

HRID 1017715Notes

Reaction equation

HRID 1017715 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-])=O)[CH:3]=1.[C:13](OCC)(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].N1CCCCC1>[Pd].C(O)C>[CH2:18]([O:17][C:15]([C:14]1[C:13](=[O:20])[NH:10][C:4]2[C:5]([CH:6]=1)=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)=[O:16])[CH3:19]

Participants

6

Reactant 3

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

Product 1

HCID 22897229HCID 22897229, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-chloro-2-nitrobenzaldehyde (9-1, 495 mg, 2.64 mmol, 1 equiv) and 10% palladium on carbon (0.280 g, 0.264 mmol, 0.100 equiv) in ethanol (20 mL) was stirred under a hydrogen balloon for 1 h at 23° C. The catalyst was filtered onto a pad of celite and washed with ethanol (20 mL). The combined filtrate was concentrated to 20 mL, then diethyl malonate (0.801 mL, 5.28 mmol, 2.00 equiv) and piperidine (0.130 mL, 1.32 mmol, 0.500 equiv) were added. The resulting mixture was heated at reflux for 5 h. The mixture was allowed to cool to 23° C., and the precipitate was filtered and washed with cold ethanol (10 mL) to give 7-chloro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (9-2) as a white solid.

Workup

  1. filtrationThe catalyst was filtered onto a pad of celite
  2. washwashed with ethanol (20 mL)
  3. concentrationThe combined filtrate was concentrated to 20 mL
  4. temperatureThe resulting mixture was heated
  5. temperatureat reflux for 5 h
  6. temperatureto cool to 23° C.
  7. filtrationthe precipitate was filtered
  8. washwashed with cold ethanol (10 mL)

Sources & evidence

ORD record
ord-a1252a0177ff40eb819cf0dc65379453
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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