Triethyl orthoacetate → 2-methyl-1-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-1H-imidazo[4,5-c]quinoline

HRID 2362519Notes

Reaction equation

HRID 2362519 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][C:12]=2[NH2:21])[O:6][CH2:5][CH2:4][O:3]1.[C:22](OCC)(OCC)(OCC)[CH3:23]>C1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH3:22][C:23]1[N:10]([CH2:9][CH2:8][CH2:7][C:2]2([CH3:1])[O:3][CH2:4][CH2:5][O:6]2)[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1

Participants

5

Reactant 2

HCID 66221Triethyl orthoacetateHCID 86052449N4-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]quinoline-3,4-diamine

Product 1

HCID 689348722-methyl-1-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-1H-imidazo[4,5-c]quinolineYield 99.6%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolvent2×

Procedure

A solution of N4-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]quinoline-3,4-diamine (6.20 g, 21.6 mmol), triethyl orthoacetate (3.10 g, 25.8 mmol) and pyridinium p-toluenesulfonate (0.18 g, 0.71 mmol) in toluene (250 mL) was heated at reflux under a Dean-Stark trap for 2 hours, periodically draining off the distillate and adding fresh toluene to the reaction mixture. The solution was concentrated under reduced pressure, and the residue was taken up in dichloromethane (150 mL), washed successively with a saturated aqueous sodium bicarbonate solution and water (100 mL each), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 2-methyl-1-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-1H-imidazo[4,5-c]quinoline (6.70 g) as a dark oil that was used directly in the next step without further purification.

Workup

  1. temperatureat reflux under a Dean-Stark trap for 2 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. washwashed successively with a saturated aqueous sodium bicarbonate solution and water (100 mL each)
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26b873b24a194ba1baddad0f4917b6cc
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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