Hydrochloric Acid → 1-(4-aminobutyl)-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1837562Notes

Reaction equation

HRID 1837562 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>CO>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 9888986HCID 9888986, compound

Product 1

HCID 121489921-(4-aminobutyl)-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amineYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The tert-butyl N-[4-(4-amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (4.3 g, 10.0 mmol) was dissolved in methanol (15 mL) and 1 N hydrochloric acid (100 mL) and then heated at reflux for 2 hours. The reaction mixture was concentrated under vacuum to a volume of about 50 mL. Addition of concentrated ammonium hydroxide to pH 12 did not produce a precipitate. The pH was adjusted to 7 with 1 N hydrochloric acid. The mixture was extracted with dichloromethane and then with ethyl acetate. The aqueous layer was concentrated to dryness. The residue was dissolved in water (50 mL) and then extracted continuously with refluxing chloroform for 36 hours. The chloroform extract was concentrated under vacuum to provide a light tan solid. This material was recrystallized from acetonitrile to provide 2.5 g of 1-(4-aminobutyl)-2-phenyl-1H-imidazo[4,5-c]quinolin4-amine as an off white solid, m.p. 175-177° C. Analysis: Calculated for C20H21N5: %C, 72.48; %H, 6.39; %N, 21.13; Found: %C, 72.72; %H, 6.32; %N, 20.71.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction mixture was concentrated under vacuum to a volume of about 50 mL
  3. additionAddition of concentrated ammonium hydroxide to pH 12
  4. customdid not produce a precipitate
  5. extractionThe mixture was extracted with dichloromethane
  6. concentrationThe aqueous layer was concentrated to dryness
  7. dissolutionThe residue was dissolved in water (50 mL)
  8. extractionextracted continuously with refluxing chloroform for 36 hours
  9. extractionThe chloroform extract
  10. concentrationwas concentrated under vacuum
  11. customto provide a light tan solid
  12. customThis material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-cc99064b31db4cf3873baab5f614e42c
Source dataset
uspto-grants-2004_08
Patent number
US06784188B2

Reaction notes

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