Sodium Bicarbonate → Theophylline

HRID 652976Notes

Reaction equation

HRID 652976 reaction equation
COC1C=C(C=CC=CC(N2CCN(CC[N:30]3[C:39]4[C:38](=[O:40])[N:36]([CH3:37])[C:35](=[O:41])[N:34]([CH3:42])[C:33]=4[N:32]=[CH:31]3)CC2)=O)C=CC=1OCOCCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[N:36]1([C:38](=[O:40])[C:39]2[NH:30][CH:31]=[N:32][C:33]=2[N:34]([CH3:42])[C:35]1=[O:41])[CH3:37]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 53719723HCID 53719723, compound

Product 1

HCID 2153Theophylline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 502 mg (0.86 mmol) of the theophylline derivative in 8 ml of methanol was added, under argon atmosphere, 360 mg (1.90 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled to room temperature, adjusted to a pH value of 10 by the addition of a saturated aqueous solution of sodium hydrogencarbonate, and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue (540 mg) was subjected to silica gel column chromatography, eluted with chloroform-methanol (50:1), to give 225 mg (0.45 mmol) of 7-[2-[4-[5-(3-methoxy-4-hydroxyphenyl)-2,4]-pentadienoyl]piperazin-1-yl]ethyl]theophylline.

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. washeluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-059e56f66d7340189abaaab0447ab1fd
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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