Trityl chloride → 3-Trityl-3H-imidazo[4,5-c]quinoline

HRID 2165545Notes

Reaction equation

HRID 2165545 reaction equation
[NH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>CC#N>[C:14]([N:3]1[C:4]2[CH:5]=[N:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[N:1]=[CH:2]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178419901HCID 178419901, compound

Product 1

HCID 146217253-Trityl-3H-imidazo[4,5-c]quinolineYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5.2 g of 1H-imidazo[4,5-c]quinoline (II-1) in 180 ml of MeCN were added 10.3 g of trityl chloride and 4.2 g of triethylamine, and the mixture was stirred at room temperature for 8 hours. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with water and brine, and then dried. The ethyl acetate was removed and the residue was chromatographed on a column of silica gel with ethyl acetate-n-hexane (1:1 v/v). Crystallization of the resulting oily substance from n-hexane gave 12.4 g (yield: 98%) of the titled compound (III-1). This was recrystallized from ethyl acetate-n-hexane to give colorless crystals melting at 190°~192° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. customThe ethyl acetate was removed
  6. customthe residue was chromatographed on a column of silica gel with ethyl acetate-n-hexane (1:1 v/v)
  7. customCrystallization of the resulting oily substance from n-hexane

Sources & evidence

ORD record
ord-3ba5063938ed48e4abf94966feffcae4
Source dataset
uspto-grants-1990_07
Patent number
US04940714

Reaction notes

Loading…