Water → HCID 18466674, compound

HRID 368367Notes

Reaction equation

HRID 368367 reaction equation
[CH3:1][C:2]1([CH3:18])[C:15]2[C:6](=[N:7][C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[N:14]=2)[C:5]([CH3:17])([CH3:16])[CH2:4][CH2:3]1.[OH2:19]>C(O)(=O)C>[CH3:1][C:2]1([CH3:18])[CH2:3][CH2:4][C:5]([CH3:17])([CH3:16])[C:6]2[N:7]=[C:8]3[C:13]([CH2:12][CH2:11][CH2:10][C:9]3=[O:19])=[N:14][C:15]1=2

Participants

4

Reactant 2

HCID 962Water2×HCID 18466766HCID 18466766, compound

Product 1

HCID 18466674HCID 18466674, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

8.0 g of 1,2,3,4,6,7,8,9-octahydro-1,1,4,4-tetramethylphenazine was dissolved in 30 ml of acetic acid, followed by the dropwise addition of a solution of 4.9 g of chromic acid anhydride in acetic acid (30 ml)/water (4 ml). The obtained mixture was stirred at 80° C. for 30 minutes, 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: 20% ethyl acetate/hexane) to give 1.6 g of the title compound as a brown oil.

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: 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9b3707fea1ca4a67b346e5ab31a32d9a
Source dataset
uspto-grants-2000_10
Patent number
US06133283

Reaction notes

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