Water → HCID 18466731, compound

HRID 368365Notes

Reaction equation

HRID 368365 reaction equation
[CH:1]([C:4]1[C:13]([CH:14]([CH3:16])[CH3:15])=[N:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1)([CH3:3])[CH3:2].[OH2:17]>C(O)(=O)C>[CH:1]([C:4]1[C:13]([CH:14]([CH3:16])[CH3:15])=[N:12][C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:17])[C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962Water2×HCID 18466650HCID 18466650, compound

Product 1

HCID 18466731HCID 18466731, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

1.5 g of 5,6,7,8-tetrahydro-2,3-diisopropyl-quinoxaline was dissolved in 10 ml of acetic acid, followed by the dropwise addition of a solution of 1.0 g of chromic acid anhydride in acetic acid (6 ml)/water (1 ml). The obtained mixture was stirred at 80° C. for 2 hours, cooled by allowing to stand, and poured into water, followed by the extraction with ethyl acetate. The organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and concentrated in a vacuum. The obtained residue was purified by silica gel chromatography (developer: 10% ethyl acetate/hexane) to give 0.6 g of the title compound as a brown solid.

Workup

  1. temperaturecooled
  2. extractionfollowed by the extraction with ethyl acetate
  3. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in a vacuum
  6. customThe obtained residue was purified by silica gel chromatography (developer: 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-28bcc01c5b984339be435b8b4a4942aa
Source dataset
uspto-grants-2000_10
Patent number
US06133283

Reaction notes

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