Acetic Acid → HCID 11107934, compound

HRID 1795398Notes

Reaction equation

HRID 1795398 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH2:19][NH2:20].C(O)(=O)C>O>[NH:19]([C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1)[NH2:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 3839614-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 11107934HCID 11107934, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (10.0 g, 0.0385 moles, U.S. Pat. No. 4,689,338 Example 77) was added to hydrazine (30 mL). The mixture heated rapidly to reflux. The solid dissolved with a vigorous heat of reaction then a precipitate formed as the reaction mixture refluxed. The reaction mixture was diluted with water. The precipitate was isolated by filtration then suspended in water (100 mL). The solid was brought into solution by the addition of acetic acid. The solution was filtered to remove traces of undissolved solid. The filtrate was made basic by the addition of ammonium hydroxide. The resulting precipitate was isolated by filtration, washed with water then dried to provide 8.0 g of crude product as a white solid. A sample of this material was recrystallized from methanol to provide 4-hydrazino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline, m.p. 202–205° C. Analysis: Calculated for C14H17N5: % C, 65.86; % H, 6.71; % N, 27.43. Found: % C, 65.20; % H, 6.6; % N, 27.5.

Workup

  1. temperatureThe mixture heated rapidly
  2. temperatureto reflux
  3. dissolutionThe solid dissolved with
  4. temperaturea vigorous heat of reaction
  5. customa precipitate formed as the reaction mixture
  6. temperaturerefluxed
  7. customThe precipitate was isolated by filtration
  8. filtrationThe solution was filtered
  9. customto remove traces of undissolved solid
  10. additionThe filtrate was made basic by the addition of ammonium hydroxide
  11. customThe resulting precipitate was isolated by filtration
  12. washwashed with water
  13. customthen dried
  14. customto provide 8.0 g of crude product as a white solid
  15. customA sample of this material was recrystallized from methanol

Sources & evidence

ORD record
ord-9e85e3011c394ff8b0afcb23cf283d42
Source dataset
uspto-grants-2006_04
Patent number
US07026482B2

Reaction notes

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