Ethyl orthopropionate → 2-ethyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline

HRID 547294Notes

Reaction equation

HRID 547294 reaction equation
[C:1](OCC)(OCC)(OCC)[CH2:2][CH3:3].[CH3:13][S:14]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=[CH:25][C:24]=1[NH2:33])(=[O:16])=[O:15].Cl.N1C=CC=CC=1>C(#N)C>[CH2:2]([C:3]1[N:22]([CH2:21][CH2:20][O:19][CH2:18][CH2:17][S:14]([CH3:13])(=[O:16])=[O:15])[C:23]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[CH:25][C:24]=2[N:33]=1)[CH3:1]

Participants

5

Reactant 3

HCID 66995Ethyl orthopropionateHCID 10176127Pyridinium chlorideHCID 86064731N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine

Product 1

HCID 672037522-ethyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinolineYield 92.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethyl orthopropionate (2.5 mL, 12 mmol) was added to a stirred solution of N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine (3.2 g, 10 mmol) in acetonitrile (50 mL). Pyridine hydrochloride (0.3 g) was added and the reaction mixture was heated to reflux with the volatiles being collected in a Dean Stark trap. After 40 minutes analysis by TLC indicated that the starting material was consumed. The reaction mixture was concentrated under reduced pressure to provide 3.2 g of 2-ethyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline as an oil which slowly solidified.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux with the volatiles
  3. custombeing collected in a Dean Stark trap
  4. customwas consumed
  5. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-322eb37ffa6c47cabf6fcc306034eb6d
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

Loading…