Triethylamine → 4-Quinolinecarboxylic acid, 1,2-dihydro-2-oxo-, methyl ester

HRID 6811

Reaction equation

HRID 6811 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C/[C:10](/[C:16]([O-:18])=[O:17])=[C:11](\C)/[C:12]([O-:14])=O.[CH2:19](N(CC)CC)C>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(#N)C>[O:14]=[C:12]1[CH:11]=[C:10]([C:16]([O:18][CH3:19])=[O:17])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 119952-IodoanilineHCID 5459894Dimethylmaleate

Product 1

HCID 1816364-Quinolinecarboxylic acid, 1,2-dihydro-2-oxo-, methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a heavy-walled PYREX tube was placed 2-iodoaniline (2.84 g, 13 mmol), dimethylmaleate (2.44 g, 17 mmol), triethylamine (1.4 mL, 10 mmol), palladium diacetate (31 mg, 0.14 mmol) and 6 mL acetonitrile. The tube was flushed with nitrogen and sealed. The sealed tube was heated at 100° for 3.5 h then cooled to r.t. The tube was opened and the resulting solids filtered and washed with acetonitrile. The solids were dissolved in chloroform and the solvent removed under vacuum to provide a solid.

Workup

  1. customThe tube was flushed with nitrogen
  2. customsealed
  3. temperatureThe sealed tube was heated at 100° for 3.5 h
  4. filtrationthe resulting solids filtered
  5. washwashed with acetonitrile
  6. dissolutionThe solids were dissolved in chloroform
  7. customthe solvent removed under vacuum
  8. customto provide a solid

Sources & evidence

ORD record
ord-ce024ddd171d42738801fd911c4752bb
Source dataset
uspto-grants-2006_08
Patent number
US07084156B2

Linked notes

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