Hydrochloric Acid → 4-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride

HRID 258818Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]([CH2:19][CH2:20][OH:21])[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.C(OC(=O)C)(=O)C.[N+:29]([O-:32])([OH:31])=[O:30].[ClH:33]>C(O)C.C(OCC)C.C(O)(=O)C>[ClH:33].[ClH:33].[N+:29]([O-:32])([OH:31])=[O:30].[N+:29]([O-:32])([OH:31])=[O:30].[OH:1][CH2:2][CH2:3][N:4]([CH2:19][CH2:20][OH:21])[CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 5.0 g. of 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline in 5.0 g. of glacial acetic acid is added slowly to a mixture of 15 ml. of acetic anhydride and 5.0 ml. of 90% nitric acid with stirring at minus 5° C. The resulting mixture is allowed to warm to plus 5° C. and after standing for an additional 5 minutes it is treated with an excess of ice-cold aqueous ammonia solution and then extracted with methylene chloride to obtain an amber oil which is dissolved in 5.0 ml. of ethanol and treated with a slight excess of hydrogen chloride in ethanol. Addition of diethyl ether yields a solid which is recrystallized from methanol/diethyl ether to obtain 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride, m.p. 125° C. (decomp.).

Workup

additionit is treated with an excess of ice-cold aqueous ammonia solution
extractionextracted with methylene chloride
customto obtain an amber oil which
dissolutionis dissolved in 5.0 ml
customyields a solid which
customis recrystallized from methanol/diethyl ether

Sources & evidence

ORD record: ord-2d21d5900dc14b8ab509d26d15560f0b
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04035367

Reaction notes

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