Methyl iodide → 10-Chloro-9-hydroxy-8-methoxy-1,4anthracenedione

HRID 620904Notes

Reaction equation

HRID 620904 reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9]([OH:17])=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]2=[O:18].[H-].[Na+].[CH3:22]I>CS(C)=O>[Cl:1][C:2]1[C:15]2[C:10](=[C:11]([O:16][CH3:22])[CH:12]=[CH:13][CH:14]=2)[C:9]([OH:17])=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]2=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 1366779410-Chloro-8,9-dihydroxy-1,4-anthracenedione2×

Product 1

HCID 1566352910-Chloro-9-hydroxy-8-methoxy-1,4anthracenedione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-Chloro-8, 9-dihydroxy-1,4-anthracenedione (compound 3) (100 mg) was dissolved with stirring in dry dimethyl sulfoxide (25 ml) under a nitrogen atmosphere. Sodium hydride (80% dispersion, 28.5 mg) was added to the solution in one aliquot. The resulting dark blue solution was stirred for 5 min then methyl iodide (156 mg, 0.1 ml) was added in one lot. Stirring was continued for 10 min then another aliquot of methyl iodide (0.1 ml) was added to the mixture. After a further 5 min the dark blue solution was quenched with ice-cold phosphate buffer (pH 7) to give a red suspension which was extracted with chloroform. The combined organic extracts were dried and evaporated to a crude solid which was chromatographed on a column of silica gel 60 with chloroform as eluant. The mobile red band gave the product (compound 12) as a red solid (84 mg, 88%).

Workup

  1. stirringStirring
  2. waitwas continued for 10 min
  3. customAfter a further 5 min the dark blue solution was quenched with ice-cold phosphate buffer (pH 7)
  4. customto give a red suspension which
  5. extractionwas extracted with chloroform
  6. customThe combined organic extracts were dried
  7. customevaporated to a crude solid which
  8. customwas chromatographed on a column of silica gel 60 with chloroform as eluant

Sources & evidence

ORD record
ord-ccae320a316a4b84942eb61488168901
Source dataset
uspto-grants-1989_04
Patent number
US04822873

Reaction notes

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