Pyridine → Des-(2-cyclohexane-1,3-dione) Fenquinotrione Ethyl Ester

HRID 1942152Notes

Reaction equation

HRID 1942152 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:12])[NH:7]2.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](OB(O)O)=[CH:22][CH:21]=1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CCCCCC.C(OCC)(=O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:12])[N:7]2[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 147699944-Methoxyphenyl boric acidHCID 67531483Ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

Product 1

HCID 67533339Des-(2-cyclohexane-1,3-dione) Fenquinotrione Ethyl EsterYield 78%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 6212ChloroformSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry containing 5.7 g (22.6 mmol) of ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate, 6.9 g (45.4 mmol) of 4-methoxyphenylboric acid, 8.2 g (45.1 mmol) of anhydrous copper (II) acetate and chloroform (200 ml), 3.6 g (45.5 mmol) of pyridine and 4.6 g (45.5 mmol) of triethylamine were added dropwise, and the mixture was stirred for 72 hours at room temperature. The reaction mixture was washed with 10% hydrochloric acid, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was isolated by silica gel chromatography (developing solvent: ethyl acetate:hexane=2:3), and the isolated solid was washed with diisopropyl ether, to obtain 6.3 g (yield: 78%) of ethyl 5-chloro-1-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a pale yellow powder.

Workup

  1. additionwere added dropwise
  2. washThe reaction mixture was washed with 10% hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. washthe isolated solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-090bc26c1a3542409874de63f2997b9f
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

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