Acetic Acid → HCID 22341064, compound

HRID 584681Notes

Reaction equation

HRID 584681 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[NH2:10].C([O:13][C:14](=O)[C:15](=O)[CH2:16][CH2:17][CH2:18][Cl:19])C.C(O)(=O)C.C(OCC)(=O)C>CN(C=O)C>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][C:5]=1[Cl:9])[NH:10][C:14](=[O:13])[C:15]([CH2:16][CH2:17][CH2:18][Cl:19])=[N:1]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 13130385Ethyl 5-chloro-2-oxopentanoate

Product 1

HCID 22341064HCID 22341064, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1,2-Diamino-4,5-dichlorobenzene (1.63 g, 9.22 mmol), dissolved in a small amount of DMF, as added dropwise to a stirred solution of 5-chloro-2-oxo-pentanoic acid ethyl ester (1.50 g, 9.22 mmol) [J. H. Hoare, P. Yates J. Org. Chem. 1983, 4, 3333] in a mixture of DMF:glacial acetic acid 7:3 (5 ml). After stirring for 3 days at room temperature, the solvent was removed in vacuo leaving a dark coloured solid. Ethyl acetate was added and the insoluble material was removed by filtration over a short pad of silica. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (ethyl acetate:heptane 25:75), to yield 25% of 6,7-dichloro-3-(3-chloropropyl)-1H-quinoxalin-2-one as a yellow solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customleaving a dark coloured solid
  3. customthe insoluble material was removed by filtration over a short pad of silica
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by flash column chromatography (ethyl acetate:heptane 25:75)

Sources & evidence

ORD record
ord-dce83a4ea33e4fc79767029c383d55d0
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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