Sulfuric Acid → HCID 58424883, compound

HRID 2409398Notes

Reaction equation

HRID 2409398 reaction equation
COC1C=CC(C[N:8]2[C:17]3[CH:18]=[CH:19][C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:21][C:16]=3[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]2=[O:27])=CC=1.C1(OC)C=CC=CC=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>CO.ClCCl.[Pd]>[O:27]=[C:9]1[NH:8][C:17]2[CH:18]=[CH:19][C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:21][C:16]=2[C:15]2[NH:14][CH2:13][CH2:12][CH2:11][C:10]1=2

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 58424929HCID 58424929, compound

Product 1

HCID 58424883HCID 58424883, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (27 mg, 0.069 mmol) prepared in step 3 was dissolved in methanol (5 ml) and dichloromethane (5 ml), and added with 10%-palladium. The mixture was stirred for 18 hours at room temperature under hydrogen gas. Once the reaction was completed, 10%-palladium (Pd) was removed by celite filter and the filtrate was concentrated under reduced pressure. The residue was dissolved in trifluoroacetic acid (TFA, 2 ml), and the resultant mixture was added with anisol (0.64 ml, 0.58 mmol) and 12 N sulfuric acid aqueous solution (0.097 ml, 1.17 mmol). The reaction mixture was stirred for 18 hours at 100° C. The mixture was stirred for one hour at 140° C. The mixture was poured into a cold sodium bicarbonate aqueous solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography (dichloromethane:methanol=7:1) to obtain the title compound (7.5 mg, yield: 47%, yellow solid).

Workup

  1. custom10%-palladium (Pd) was removed by celite
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in trifluoroacetic acid (TFA, 2 ml)
  5. stirringThe reaction mixture was stirred for 18 hours at 100° C
  6. stirringThe mixture was stirred for one hour at 140° C
  7. extractionextracted with chloroform
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash column chromatography (dichloromethane:methanol=7:1)

Sources & evidence

ORD record
ord-0943c01721b1494bbed490df8e1029f6
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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