METHOD OF SYNTHESIS OF (±) -6- CYANO- 3,4- DIHYDRO -2,2-DIMETHYL -TRANS -4- (2-HYDROXO -1-PYRROLIDINYL) -2H-1- BENZOPYRAN -3-OL Russian patent published in 1995 - IPC

Abstract RU 2036196 C1

FIELD: organic chemistry. SUBSTANCE: product: (±) -6-cyano- 3,4- dihydro-2,2-dimethyl-trans -4-(2-hydroxo-1-pyr- rolidinyl)-2H-1- benzopyran-3-ol (cromacalim). Reagent 1: 4-cyanophenol. Reagent 2: isoprene. Process conditions: at 30-120 C in solvent medium in the presence of alkaline metal and/or catalyst. Reagent 3: 6- cyano -3,4- dihydro - 2,2- dimethyl -2H-1- benzopyran at 40-150 C is brominated at position 4 of benzenepyran ring. Reagent 4: (±) -4- bromo-6- cyano - 3,4- dihydro -2,2- dimethyl -2H-1- benzopyran is dihydrobrominated. Reagent 5: 6- cyano- 3,4-dihydro -2,2- dimethyl -2H-1- benzopyran. Reagent 6: N-bromosuccinimide. Process conditions: in solvent medium at 20-120 C. Reagent 7: 6-cyano -3,4- dihydro- 2,2- dimethyl -trans-3- bromo-4- hydroxo -2H-1- -benzopyran. Reagent 8: 2-pyrrolidone. Process conditions: in the presence of alkaline metal or alkaline metal alcoholate at 20-100 C. Yield of the end product is 55-65%. Synthesized compound is used in medicine. EFFECT: improved method of synthesis, increased yield. 11 cl

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RU 2 036 196 C1

Authors

Tibor Timar[Hu]

Tibor Ehsen'I[Hu]

Peter Shebok[Hu]

Vilmosh Galamb[Hu]

Julia Fazekash[Hu]

Terezia Ishtvan[Hu]

Eva Kovach[Hu]

Ehrika Nad'[Hu]

Dates

1995-05-27Published

1990-07-20Filed