Hydrochloric Acid → 5-Hydrazinoquinoline dihydrochloride

HRID 353447Notes

Reaction equation

HRID 353447 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[N:13]([O-])=O.[Na+].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.C(O)(=O)C(O)=O>O>[ClH:1].[ClH:1].[NH:2]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2)[NH2:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 971Oxalic AcidHCID 119115-AminoquinolineHCID 23668193Sodium NitriteHCID 54670067L-Ascorbic Acid

Product 1

HCID 123341075-Hydrazinoquinoline dihydrochlorideYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-1 °C

Procedure

To a 250 ml flask under a nitrogen atmosphere, water (20 ml) and concentrated HCl (60 ml, 0.61 moles) were charged and cooled down to −2 to 0° C. 5-Aminoquinoline (10 g, 0.069 moles) was added in one portion as a solid. An increase in temperature of 10° C. was observed. The orange-yellow suspension was re-cooled to −2 to 0° C. and sodium nitrite (5.8 g, 0.084 moles) dissolved in water (10 ml) was added dropwise to the acidic solution through an addition funnel over a period of 20 minutes at −2 to 0° C. The resulting mixture (dark-brown solution) was stirred for 1 hour at −2 to 0° C. L-Ascorbic acid (14.3 g, 0.081 moles) was then added in portions as a solid over a period of 20 minutes at −2 to 0° C. The reaction was allowed to come to room temperature (18-20° C.) over a period of 30 minutes, then heated at 50° C. and stirred for 30 hours at this temperature. The resultant slurry was cooled to room temperature (18-20° C.), stirred for 1 hour at this temperature, filtered and washed with propan-2-ol (40 ml). The product was dried to constant weight in an air tray drier at 40° C. to afford 11.75 g of 5-hydrazinoquinoline dihydrochloride as a green solid (HPLC purity calculated as area percent: 98%, with 1.6% of oxalic acid intermediate; 71.5% molar yield).

Workup

  1. temperatureAn increase in temperature of 10° C.
  2. temperatureThe orange-yellow suspension was re-cooled to −2 to 0° C.
  3. additionwas added dropwise to the acidic solution through an addition funnel over a period of 20 minutes at −2 to 0° C
  4. customto come to room temperature
  5. custom(18-20° C.)
  6. customof 30 minutes
  7. temperatureheated at 50° C.
  8. stirringstirred for 30 hours at this temperature
  9. temperatureThe resultant slurry was cooled to room temperature (18-20° C.)
  10. stirringstirred for 1 hour at this temperature
  11. filtrationfiltered
  12. washwashed with propan-2-ol (40 ml)
  13. customThe product was dried to constant weight in an air tray drier at 40° C.
  14. customto afford

Sources & evidence

ORD record
ord-21456aaa37214b5b9a5f864994800cd9
Source dataset
uspto-grants-2004_06
Patent number
US06753334B2

Reaction notes

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