Methanol → HCID 21075717, compound

HRID 1373928Notes

Reaction equation

HRID 1373928 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH3:2].Cl.N1C=CC=CC=1.CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:18]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 10176127Pyridinium chlorideHCID 21075718HCID 21075718, compound

Product 1

HCID 21075717HCID 21075717, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent2×

Procedure

A suspension of 2-ethoxy-N-{4-[(morpholin-4-yl)amino]quinolin-3-yl}acetamide (5.35 g, 16.2 mmol) in 65 mL of toluene was treated with pyridine hydrochloride (0.94 g g, 0.081 mmol). The reaction flask was equipped with a Dean-Stark trap and the reaction mixture was heated to reflux under an atmosphere of nitrogen. After 2.5 d, the reaction mixture was concentrated under reduced pressure to yield a brown oil. The oil was dissolved in CHCl3 and was washed with 5% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a brown foam. Chromatography (SiO2, 95:5 CHCl3:MeOH) gave 2-ethoxymethyl-1-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline (1.61 g) as a light brown solid.

Workup

  1. customThe reaction flask was equipped with a Dean-Stark trap
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux under an atmosphere of nitrogen
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customto yield a brown oil
  6. washwas washed with 5% Na2CO3 solution, water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a brown foam

Sources & evidence

ORD record
ord-11fab72d1135482f84882f2f6efc66db
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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