Tetrahydrofuran → HCID 19706756, compound

HRID 726634Notes

Reaction equation

HRID 726634 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:5]=1[CH:6]=O)([O-])=O.[H][H].[C:18]([O:24]CC)(=[O:23])[CH2:19][C:20]([CH3:22])=O.[CH2:27]1COC[CH2:28]1>N1CCCCC1.[Ni]>[CH2:27]([C:6]1[C:5]2[C:4](=[CH:11][C:10]([O:12][CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=2)[N:1]=[C:20]([CH3:22])[C:19]=1[C:18]([OH:24])=[O:23])[CH3:28]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8868Ethyl AcetoacetateHCID 885056-NitroveratraldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 19706756HCID 19706756, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8082PiperidineCatalyst

Procedure

A mixture of 2-nitro-4,5-dimethoxybenzaldehyde (5.28 g, 25 mmol) and Raney-nickel in THF (100 ml) was hydrogenated until three equivalents of hydrogen had been consumed. The mixture was filtered through Celite. Ethyl acetoacetate (3.2 ml, 25 mmol) and piperidine (12 drops) were added and the solution was refluxed for 4 h and concentrated. The solid residue was recrystallized from MeOH to give 3.89 g ethyl 6,7-dimethoxy-2-methylquinoline-3-carboxylic acid.

Workup

  1. customhad been consumed
  2. filtrationThe mixture was filtered through Celite
  3. temperaturethe solution was refluxed for 4 h
  4. concentrationconcentrated
  5. customThe solid residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-4455030ed1c54864a5952cabaab72b09
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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