1,4-Dioxane → HCID 15662876, compound

HRID 487735Notes

Reaction equation

HRID 487735 reaction equation
C([O:8][C:9]1[C:10]([O:32][CH3:33])=[C:11]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[C:18]1[C:17]([OH:24])=[C:16]([O:25][CH3:26])[C:15]([O:27][CH3:28])=[C:14]([O:29][CH3:30])[C:13]=1[N:12]2C)C1C=CC=CC=1.O1CCOCC1>C(O)C.[Pd]>[OH:24][C:17]1[C:18]2[C:19](=[O:23])[C:20]3[C:11](=[C:10]([O:32][CH3:33])[C:9]([OH:8])=[CH:22][CH:21]=3)[NH:12][C:13]=2[C:14]([O:29][CH3:30])=[C:15]([O:27][CH3:28])[C:16]=1[O:25][CH3:26]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 15662873HCID 15662873, compound

Product 1

HCID 15662876HCID 15662876, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-benzyloxy-1-hydroxy-10-methyl-2,3,4,5-tetramethoxy-9-acridone (344 mg, 0.76 mmol) in ethanol (80 ml) containing dioxane (20 ml) and 10% palladium on carbon (200 mg) was hydrogenated at 50 psi for 2.5 hours. The mixture was filtered through a pad of Celite and washed well with ethanol and chloroform. The combined filtrate and washings were evaporated in vacuo to dryness. The solid residue was recrystallized from a mixture of ethanol/hexane (2:3) to give 1,6-Dihydroxy-2,3,4,5-tetramethoxy-9-acridone, 222 mg (80.7%), mp 214-5 ° C. 1H-NMR (DMSO-d6): δ3.69, 3.75, 3.78, 3.80, and 4.02 (each 3H, s, 4×OMe, 1×NMe), 6.94 (1H, d, J=9.0 Hz, H-7), 7.84 (1H, d, J =9.0 Hz, H-8), 10.45 (1H, exchangeable, OH-6), 14.18 (lH, exchangeable, OH-1). Analyses: Calculated for C18H19NO7 : C, 59.83; H, 5.30; N, 3.88. Found C, 60.00, H, 5.38; N, 4.00.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashed well with ethanol and chloroform
  3. customThe combined filtrate and washings were evaporated in vacuo to dryness
  4. customThe solid residue was recrystallized from a mixture of ethanol/hexane (2:3)

Sources & evidence

ORD record
ord-7dc0906511a54b2a882e9425f8c7dbca
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

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