Ammonia → 2-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride

HRID 1076641Notes

Reaction equation

HRID 1076641 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[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.C(OC(=O)C)(=O)C.[N+:29]([O-:32])([OH:31])=[O:30].N.[ClH:34]>C(O)C.C(OCC)C.C(O)(=O)C>[ClH:34].[ClH:34].[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[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 214246762-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline

Product 1

HCID 867334282-[3-Bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5.0 g. of 2-[3-bis(2-hydroxyethyl)aminopropyl] amino-quinoline in 5.0 g. of glacial acetic acid is added slowly to a stirred cooled (-5°C.) mixture of 15.0 ml. of acetic anhydride and 5.0 ml. of 90% nitric acid. Stirring is continued for 20 minutes after addition and 500 ml. of diethyl ether added to obtain an oil which is added to an excess of cooled (0°C.) aqueous ammonia solution. The resulting mixture is extracted with ethyl acetate, the organic phase dried and concentrated in vacuo to obtain an oil which is 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 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline dinitrate dihydrochloride, m.p. 112°C. (decomp.)

Workup

  1. temperaturecooled
  2. addition(-5°C.) mixture of 15.0 ml
  3. additionafter addition and 500 ml
  4. customto obtain an oil which
  5. additionis added to an excess
  6. extractionThe resulting mixture is extracted with ethyl acetate
  7. customthe organic phase dried
  8. concentrationconcentrated in vacuo
  9. customto obtain an oil which
  10. customyields a solid which
  11. customis recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-daed2a3183dd47028007df777a4008ea
Source dataset
uspto-grants-1976_05
Patent number
US03957791

Reaction notes

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