Trifluoroacetic acid → 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline

HRID 1108631Notes

Reaction equation

HRID 1108631 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([Cl:25])[C:15]=2[N:14]=[CH:13]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([Cl:25])[C:15]=2[N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 187839501-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline

Product 1

HCID 177767961-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinolineYield 38.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (0.139 mg) of 1-[3-(tert-butoxycarbonylamino)-propyl]-4-chloro-1H-imidazo[4,5-c]quinoline was dissolved in 3 ml of methylene chloride. 0.11 ml (1.39 mmol) of trifluoroacetic acid was added thereto and the mixture was stirred at room temperature for one day. The reaction mixture was concentrated under reduced pressure and 1 ml of a 1N sodium hydroxide aqueous solution and brine were added to the residue. The resulting solution was extracted with chloroform five times, thereafter the extract was dried (Na2SO4), and concentrated under reduced pressure. The residue was triturated with diethyl ether (containing a small amount of methylene chloride) and the precipitate thus formed was collected by filtration to obtain 14 mg (0.0536 mmol) of 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline shown below as white powder. ##STR37## Its spectroscopic data are as follows: IR (KBr) cm- 1 : 340, 1590, 1510. 1H-NMR (CDCl3 +CD3OD) 5 (ppm) : 2.06 (2H, m), 2.72 (2H, t, J=6.8 Hz), 2.98 (2H, b r), 4.64 (2H, t, J=7.0 Hz), 7.57 (1H, t, J=7.6 Hz), 7.61 (1H, t, J=7.6 Hz), 8.03 (1H, s), 8.05 (1H, d, J=8.0 Hz), 8.11 (1H, d, J=8.0 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 1 ml of a 1N sodium hydroxide aqueous solution and brine
  2. additionwere added to the residue
  3. extractionThe resulting solution was extracted with chloroform five times
  4. dry with materialthe extract was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with diethyl ether (
  7. additioncontaining a small amount of methylene chloride) and the precipitate
  8. customthus formed
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-394ab66bc3344e5b9d41e78a732d113f
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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