Nitric Acid → Isosorbide Mononitrate

HRID 1735679Notes

Reaction equation

HRID 1735679 reaction equation
CC([O:4][C@@H:5]1[C@H:9]2[O:10][CH2:11][C@@H:12]([OH:13])[C@H:8]2[O:7][CH2:6]1)=O.[N+:14]([O-])([OH:16])=[O:15].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(OC(=O)C)(=O)C.CO>[CH2:11]1[O:10][C@@H:9]2[C@H:5]([O:4][N+:14]([O-:16])=[O:15])[CH2:6][O:7][C@@H:8]2[C@H:12]1[OH:13]

Participants

7

Reactant 3

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 10856233Isosorbide-2-Acetate

Product 1

HCID 27661Isosorbide Mononitrate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 7918Acetic AnhydrideSolvent

Procedure

For this isosorbide-2-acetate is for example firstly nitrated with nitric acid in glacial acetic acid or acetic acid anhydride and subsequently the acetate group is cleaved off with potassium carbonate in methanol. In this process isosorbide-5-nitrate is obtained in an isomerically pure form and in excellent yield (FIG. 1).

Sources & evidence

ORD record
ord-5c0e6cbd81b24705889798c2a33ccf82
Source dataset
uspto-grants-1996_07
Patent number
US05538891

Reaction notes

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