Synthesis of 4-amino-1,2-hydrocarbyl pyrazolidines via 4-nitro analogs
AssigneeA. H. Robins Company, Incorporated
InventorsYoung S. Lo, Harry R. Munson, Jr.
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Abstract
4-Nitro-1,2-hydrocarbyl pyrazolidines are prepared by a novel route from 1,2-disubstituted hydrazines and 1,3-di-(secondary amino)-2-nitropropanes and reduced to the corresponding 4-amino-1,2-hydrocarbyl pyrazolidines, which latter compounds are intermediates in the preparation of certain pharmaceutical benzamides. The novel 4-nitro-1,2-hydrocarbyl pyrazolidines have the formula: ##STR1## wherein R.sup.1 and R.sup.2 are selected from loweralkyl, lowercycloalkyl or phenyl-loweralkyl and may be the same or different.
Claims5
A process for the preparation of 4-amino-1,2-hydrocarbyl pyrazolidines having the formula:
- ##STR6## wherein;
- R.sup.1 and R.sup.2 are loweralkyl radicals containing from one to eight carbons, cyclic alkyl radicals containing from three to twelve carbons or phenylloweralkyl wherein the loweralkyl group contains from one to eight carbons and phenyl may be substituted with a nonreactive radical selected from the group consisting of lower alkyl, lower alkoxy, trifluoromethyl, halo, acetamido and sulfamoyl and may be the same or different, which comprises the steps of
- (1) reacting a disubstituted hydrazine acid salt having the formula:
- R.sup.1 NH-NHR.sup.2.2HX
- wherein R.sup.1 and R.sup.2 are as defined above and X is an acid anion, with a 1,3-bis(disubstituted amino)-2-nitropropane having the formula:
- R.sup.3 R.sup.4 NCH.sub.2 CHNO.sub.2 CH.sub.2 NR.sup.5 R.sup.6
- wherein R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are loweralkyl radicals containing from one to eight carbon atoms and may be the same or different and R.sup.3 and R.sup.4 or R.sup.5 and R.sup.6 taken together with the adjacent nitrogen atom may form a heterocyclic residue selected from the group consisting of pyrrolidino, morpholino, piperidino and piperazino in the presence of a solvent therefor and at a temperature between room temperature and 150.degree. C., to produce a 4-nitro-1,2-hydrocarbyl-pyrazolidine having the formula:
- ##STR7## wherein R.sup.1 and R.sup.2 are as defined above, and (2) reducing said 4-nitro-1,2-hydrocarbyl-pyrazolidine to produce said 4-amino-1,2-hydrocarbyl-pyrazolidine.
Dependencies are inferred from the claim text.