Acetone Cyanohydrin → HCID 178492039, compound

HRID 240331Notes

Reaction equation

HRID 240331 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:21]([OH:23])=O)[C:6](=[O:20])[N:7]2[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C(Cl)(=O)C(Cl)=O.[C:30]1(=[O:37])[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[CH2:31]1.C(N(CC)CC)C.CC(C)(O)C#N>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:21]([C:31]1[C:32](=[O:36])[CH2:33][CH2:34][CH2:35][C:30]=1[OH:37])=[O:23])[C:6](=[O:20])[N:7]2[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 104341,3-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 675332908-Chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carboxylic acid

Product 1

HCID 178492039HCID 178492039, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent3×HCID 6228DimethylformamideSolvent

Procedure

6.7 g (20 mmol) of 5-chloro-1-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylic acid was dissolved in chloroform (300 mL), and to this solution, N,N-dimethylformamide (0.5 mL) and 5.2 g (41 mmol) of oxalyl chloride were added sequentially. The mixture was stirred for one hour at room temperature. After confirming the completion of the reaction, the solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in chloroform (70 mL), and this solution was added dropwise at 0° C. over 5 minutes to a solution prepared by dissolving 2.5 g (22 mmol) of 1,3-cyclohexanedione and 2.5 g (25 mmol) of triethylamine in chloroform (70 mL). The reaction solution was returned to room temperature and stirred for 3 hours, and then 0.86 g (10 mmol) of acetone cyanohydrin and 2.5 g (25 mmol) of triethylamine were added thereto. The mixture was stirred for 12 hours at room temperature. The reaction solution was washed with 10% hydrochloric acid and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue thus obtained was washed with ethyl acetate, to obtain 6.0 g (yield: 70%) of 5-chloro-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-(4-methoxyphenyl)quinoxalin-2(1H)-one as a pale orange-colored powder.

Workup

  1. customthe completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. additionthis solution was added dropwise at 0° C. over 5 minutes to a solution
  5. customprepared
  6. customwas returned to room temperature
  7. stirringstirred for 3 hours
  8. stirringThe mixture was stirred for 12 hours at room temperature
  9. washThe reaction solution was washed with 10% hydrochloric acid
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue thus obtained
  13. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-2485e3478c634664ad78acf40031612b
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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