Triethylamine → Ethyl 8-aminoquinoline-3-carboxylate

HRID 613474Notes

Reaction equation

HRID 613474 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]2Cl.C(N(CC)CC)C.[H][H]>[Pd].O1CCOCC1>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 212500758-Amino-4-chloro-3-ethoxycarbonylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 21250128Ethyl 8-aminoquinoline-3-carboxylateYield 63.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-amino-4-chloro-3-ethoxycarbonylquinoline (45 mg), triethylamine (0.026 ml) and 10%o palladium on carbon (15 mg) in dioxane was stirred for 7 hours at ambient temperature under 3 atmospheric pressure of hydrogen. Insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-dichloromethane) to give 8-amino-3-ethoxycarbonylquinoline (24.5 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-0dfc0bce7dc54ab9945cc7f95e7730a3
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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