Sulfuric Acid → HCID 10856765, compound

HRID 703482Notes

Reaction equation

HRID 703482 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])N1C1C=CC=CC=1.S(=O)(=O)(O)O.[C:23](=[O:26])(O)[O-].[Na+].[CH2:28]([O:30]CC)C.[CH3:33]CCCCC>CO>[CH3:28][O:30][C:4]([C:5]1[C:10]([CH:2]([O:1][CH3:33])[O:26][CH3:23])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 100139217H-Pyrrolo[3,4-b]pyridin-7-one, 5,6-dihydro-5-hydroxy-6-phenyl-HCID 21584099Diethylether hexane

Product 1

HCID 10856765HCID 10856765, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5,6-dihydro-5-hydroxy-6-phenyl-7H-pyrrolo[3,4-b]pyridin-7-one (1.99 g) in 100 mL of methanol was added concentrated sulfuric acid (6 mL). The reaction mixture was warmed to 75° C. for 3 hours. TLC indicated that all starting material had been converted. The reaction mixture was neutralized with aqueous sodium bicarbonate and evaporated in vacuo to remove the methanol. The aqueous residue was extracted with ether (3×). The organic extracts were combined, dried (K2CO3) and evaporated. The product was isolated by flash chromatography on silica gel using ethyl ether/hexane (3/2) as eluant to yield 1.02 g (59.4%).

Workup

  1. customevaporated in vacuo
  2. customto remove the methanol
  3. extractionThe aqueous residue was extracted with ether (3×)
  4. dry with materialdried (K2CO3)
  5. customevaporated
  6. customThe product was isolated by flash chromatography on silica gel
  7. customto yield 1.02 g (59.4%)

Sources & evidence

ORD record
ord-7a3b83fcf32e40c9aab959e7cc2d4ce0
Source dataset
uspto-grants-1991_01
Patent number
US04983612

Reaction notes

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