Acetone Cyanohydrin → HCID 178516093, compound

HRID 240335Notes

Reaction equation

HRID 240335 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=[C:13]([C:21](Cl)=[O:22])[C:12]3=[O:24])[CH:9]=[CH:10][C:2]1=2.[C:25]1(=[O:32])[CH2:30][CH2:29][CH2:28][C:27](=[O:31])[CH2:26]1.C(N(CC)CC)C.CC(C)(O)C#N.[OH-].[Na+]>ClCCl.O>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=[C:13]([C:21]([C:26]4[C:27](=[O:31])[CH2:28][CH2:29][CH2:30][C:25]=4[OH:32])=[O:22])[C:12]3=[O:24])[CH:9]=[CH:10][C:2]1=2

Participants

8

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 104341,3-CyclohexanedioneHCID 14798Sodium HydroxideHCID 86643864HCID 86643864, compound

Product 1

HCID 178516093HCID 178516093, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

The 1-(2,3-dihydrobenzo[b]1,4-dioxin-6-yl)-2-oxo-1,2-dihy droquinoxaline-3-carbonyl chloride thus obtained was dissolved in dichloromethane (30 mL), and this solution was added dropwise at 0° C. over 5 minutes to a solution prepared by dissolving 4.2 g (37 mmol) of 1,3-cyclohexanedione and 6.2 g (61 mmol) of triethylamine in dichloromethane (30 mL). The reaction solution was returned to room temperature and stirred for 3 hours, and then acetone cyanohydrin (1 mL) and 6.2 g (61 mmol) of triethylamine were added thereto. The mixture was stirred for 12 hours at room temperature. After confirming the completion of the reaction, water (50 mL) was added to the reaction solution, the reaction solution was adjusted to pH 12 using a 10% aqueous solution of sodium hydroxide, and the reaction solution was separated. The aqueous layer was adjusted to pH 1 by adding 6 N hydrochloric acid, and then the aqueous layer was extracted with dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue thus obtained was washed with methanol, to obtain 5.2 g (yield: 40%) of 1-(2,3-dihydrobenzo[b]1,4-dioxin-6-yl)-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-quinoxalin-2(1H)-one as milky white crystals.

Workup

  1. additionthis solution was added dropwise at 0° C. over 5 minutes to a solution
  2. customprepared
  3. customwas returned to room temperature
  4. stirringThe mixture was stirred for 12 hours at room temperature
  5. additionwas added to the reaction solution
  6. customthe reaction solution was separated
  7. additionby adding 6 N hydrochloric acid
  8. extractionthe aqueous layer was extracted with dichloromethane
  9. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue thus obtained
  12. washwas washed with methanol

Sources & evidence

ORD record
ord-871e741be51e4ad2a980aab0db8ecf05
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

Loading…