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
Title | Year | Author | Number |
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PROCESS FOR PREPARING (±)-6-CYANO-3,4-DIHYDRO-2,2- DIMETHYL-TRANS-4-(2-OXO-1-PYRROLIDINYL)-2H-1-BENZOPYRAN- 3-OL | 1992 |
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Authors
Dates
1995-05-27—Published
1990-07-20—Filed