Hydrochloric Acid → HCID 19821694, compound

HRID 1030060Notes

Reaction equation

HRID 1030060 reaction equation
C([C:4]1[C:9](=[O:10])[C:8]([CH3:11])=[C:7]([CH3:12])[C:6](=[O:13])[C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)C.[BH4-].[Na+].Cl.I([O-])(=O)(=O)=O.[Na+].O1CCC[CH2:31]1.O>CO.O.C(OCC)(=O)C>[CH2:15]([NH:14][C:5]1[C:6](=[O:13])[C:7]([CH3:12])=[C:8]([CH3:11])[C:9](=[O:10])[CH:4]=1)[C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:31]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21881883Oxolane--water (1/1)HCID 23667635Sodium periodateHCID 178467134HCID 178467134, compound

Product 1

HCID 19821694HCID 19821694, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the 3-acetyl-2-anilino-5,6-dimethyl-1,4-benzoquinone (700 mg, 2.6 mmol) in tetrahydrofuran-water (5:4, 12.5 mL) was added sodium borohydride (197 mg, 5.2 mmol) at room temperature. The mixture was stirred at room temperature for 10 minutes. 1N hydrochloric acid (1 mL) and ethyl acetate (50 mL) were added and the mixture was stirred for 10 minutes. The organic layer was washed with sodium bicarbonate solution and brine. The solution was dried over magnesium sulfate and concentrated in vacuo to give pale red oil. This product was dissolved in methanol (7 mL). To the solution was added sodium periodate in water at room temperature. The mixture was stirred for 5 minutes then extracted with ethyl acetate (50 mL) and washed with brine (10 mL×4). The solution was dried over magnesium sulfate and concentrated in vacuo to give a dark red oil. This was subjected to a silica gel column eluted with ethyl acetate hexane (1:3.5). The desired red color fraction was crystallized from hexane-diisopropyl ether to give red powder of the title compound (380 mg, 54% yield). Mp 101.2°-101.6° C.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. washThe organic layer was washed with sodium bicarbonate solution and brine
  3. dry with materialThe solution was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give pale red oil
  6. stirringThe mixture was stirred for 5 minutes
  7. extractionthen extracted with ethyl acetate (50 mL)
  8. washwashed with brine (10 mL×4)
  9. dry with materialThe solution was dried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customto give a dark red oil
  12. washeluted with ethyl acetate hexane (1:3.5)
  13. customThe desired red color fraction was crystallized from hexane-diisopropyl ether

Sources & evidence

ORD record
ord-fb7a5eb33c44413b9b3c7207841034ae
Source dataset
uspto-grants-1992_04
Patent number
US05104874

Reaction notes

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