Triethylamine → 4-Dimethylamino-3-ethoxycarbonyl-8-nitroquinoline

HRID 613456Notes

Reaction equation

HRID 613456 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl.[CH3:21][NH:22][CH3:23].C(N(CC)CC)C>O1CCOCC1.C(OCC)(=O)C>[CH3:21][N:22]([CH3:23])[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11196760Ethyl 4-chloro-8-nitroquinoline-3-carboxylate

Product 1

HCID 195925994-Dimethylamino-3-ethoxycarbonyl-8-nitroquinolineYield 59.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-3-ethoxycarbonyl-8-nitroquinoline (199 mg), dimethylamine hydrochloride (63.6 mg) and triethylamine (78.9 mg) in dioxane was refluxed for 3 hours. After cooling, the mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane, 1:2, v/v) to give 4-dimethylamino-3-ethoxycarbonyl-8-nitroquinoline (122 mg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-cb555853a18d436db5f4b5b2c67ecf58
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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