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US 4,065,488 AGranted
Process for preparing 1,4:3,6-dianhydro-D-glucitol 2-nitrate
AssigneeAmerican Home Products Corporation
InventorsChih H. Chou, Gordon S. Myers
Life of this patent
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Abstract
The following process for preparing 1,4:3,6-dianhydro-D-glucitol 2-nitrate is described: acylating 1,4:3,6-dianhydro-D-glucitol with 0.5 to 1.5 molar equivalents of acetic anhydride in the presence of an acid catalyst, nitrating the product so obtained with a mixture of nitric acid and acetic anhydride, hydrolyzing the product so obtained in the presence of an inorganic base and isolating 1,4:3,6-dianhydro-D-glucitol 2-nitrate. The 1,4:3,6-dianhydro-D-glucitol 2-nitrate is useful as a coronary vasodilator.
Claims6
A process for preparing 1,4:3,6-dianhydro-D-glucitol 2-nitrate which comprises the steps of:
- a. acetylating 1,4:3,6-dianhydro-D-glucitol with 0.5 to 1.5 molar equivalents of acetic anhydride in the presence of an acid catalyst to obtain a mixture of 1,4:3,6-dianhydro-D-glucitol 5-acetate, 1,4:3,6-dianhydro-D-glucitol 2-dianhydro-D-glucitol 2,5-diacetate;
- b. nitrating the latter mixture with a mixture of nitric acid and acetic anhydride to obtain a mixture of 1,4:3,6-dianhydro-D-glucitol 5-acetate 2-nitrate, 1,4:3,6-dianhydro-D-glucitol 2-acetate 5-nitrate and 1,4:3,6-dianhydro-D-glucitol 2,5-diacetate;
- and
- c. hydrolyzing the latter mixture in the presence an aqueous solution of an inorganic base to obtain a mixture of 1,4:3,6-dianhydro-D-glucitol 2-nitrate and 1,4:3,6-dianhydro-D-dlucitol 5-nitrate in a ratio greater than 2:1 and isolating 1,4:3,6-dianhydro-D-glucitol 2-nitrate.
1 more element
Dependencies are inferred from the claim text.