Methyl iodide → HCID 15662867, compound

HRID 487734Notes

Reaction equation

HRID 487734 reaction equation
[CH2:1]([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]([O:24][CH3:25])=[C:16]([O:26][CH3:27])[C:15]([O:28][CH3:29])=[C:14]([O:30][CH3:31])[C:13]=1[NH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH2:1]([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]([O:24][CH3:25])=[C:16]([O:26][CH3:27])[C:15]([O:28][CH3:29])=[C:14]([O:30][CH3:31])[C:13]=1[N:12]2[CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15662866HCID 15662866, compound

Product 1

HCID 15662867HCID 15662867, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-benzyloxy-1,2,3,4,5-pentamethoxy-9-acridone (2.257 g, 5 mmol), K2CO3 (3.0 g) and methyl iodide (2.128 g, 15 mmol) in acetone (60 ml) was heated under reflux for 20 hours. After cooling to room temperature, the mixture was filtered and washed with acetone. The combined filtrate and washings are evaporated in vacuo to dryness. The residue was dissolved in chloroform (60 ml), and the solution is washed with water (30 ml×3), dried over sodium sulfate, and concentrated to dryness. The residue was crystallized from ethanol to give 6-benzyloxy-10-methyl-1,2,3,4,5-pentamethoxy-9-acridone, 2.007 g (89%), mp 127-8 ° C. 1H-NMR (CDCl3): δ3.70, 3.87, 3.91, 3.93, 3.98, and 4.10 (each 3H, s, 5×OMe, 1×NMe), 5.24 (2H, s, CH2), 6.96 (1H, d, J=9.05 Hz, H-7), 7.32- 7.48 (5H, m Ph), 8.01 (1H, d, J=9.05, H-8). Analyses: Calculated for C25H27NO7 : C, 66.21; H, 6.00; N, 3.09. Found: C, 65.99; H, 6.18; N, 3.11.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. filtrationthe mixture was filtered
  4. washwashed with acetone
  5. customThe combined filtrate and washings are evaporated in vacuo to dryness
  6. dissolutionThe residue was dissolved in chloroform (60 ml)
  7. washthe solution is washed with water (30 ml×3)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-9d4698cee72a4fabb4bef8ca550ed594
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

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