Hydrochloric Acid → HCID 178516094, compound

HRID 240333Notes

Reaction equation

HRID 240333 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([C:20](Cl)=[O:21])[C:11]3=[O:23])=[CH:9][C:4]=2[O:3][CH2:2]1.[C:24]1(=[O:31])[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]1.C(N(CC)CC)C.Cl>ClCCl.CC(C)(O)C#N.O.CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([C:20]([C:25]4[C:26](=[O:30])[CH2:27][CH2:28][CH2:29][C:24]=4[OH:31])=[O:21])[C:11]3=[O:23])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 104341,3-CyclohexanedioneHCID 86643863HCID 86643863, compound

Product 1

HCID 178516094HCID 178516094, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 6406Acetone CyanohydrinCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

The 1-(benzo[d][1,3]dioxol-5-yl)-2-oxo-1,2-dihydroquinoxaline-3-carbonyl chloride thus obtained was dissolved in dichloromethane (30 mL), and the solution was added dropwise to a liquid mixture containing 2.7 g (24 mmol) of 1,3-cyclohexanedione, 3.7 g (36 mmol) of triethylamine and dichloromethane (20 mL), under ice-cooling. After stirring the reaction solution for 3 hours at room temperature, 0.04 g (0.53 mmol) of acetone cyanohydrin and 3.7 g (36 mmol) of triethylamine were added to the liquid mixture, and the mixture was stirred for 12 hours at room temperature. The reaction solution was poured into water, and the aqueous layer was acidified with 10% hydrochloric acid, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, and the inorganic matter was separated by filtration. The solvent was distilled off under reduced pressure, and to the residue thus obtained, a mixed solution of methanol and water was added to obtain a solid. The solid was collected by filtration and dried, to obtain 5.5 g (yield: 75%) of 1-(benzo[d][1,3]dioxol-5-yl)-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-quinoxalin-2(1H)-one as a yellow amorphous matter.

Workup

  1. additionthe solution was added dropwise to a liquid mixture
  2. temperatureunder ice-cooling
  3. stirringthe mixture was stirred for 12 hours at room temperature
  4. extractionextracted with dichloromethane
  5. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  6. customthe inorganic matter was separated by filtration
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto the residue thus obtained
  9. customto obtain a solid
  10. filtrationThe solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-3cafc538acfd4c18b28639f2923249dc
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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