Triethylamine → HCID 21075814, compound

HRID 1373912Notes

Reaction equation

HRID 1373912 reaction equation
[CH3:1][N:2]([CH3:15])[NH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][C:5]=1[NH2:14].C(N(CC)CC)C.[CH2:23]([O:25][CH2:26][C:27](Cl)=O)[CH3:24].CO.C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][N:2]([CH3:15])[N:3]1[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=[C:24]1[CH2:23][O:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 84189Ethoxyacetyl chlorideHCID 21075744HCID 21075744, compoundHCID 21584188Chloroform methanol

Product 1

HCID 21075814HCID 21075814, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2,2-dimethylhydrazino)quinolin-3-amine (4.64 g, 23.0 mmol) in 75 mL of CH2Cl2 was cooled to 0° C. under an atmosphere of nitrogen. The reaction mixture was treated with triethylamine (6.72 mL, 48.2 mmol) followed by dropwise addition of ethoxyacetyl chloride (2.95 g, 24.1 mmol). After 1.5 h, the reaction mixture was concentrated under reduced pressure. The resulting oil was dissolved in 75 mL of ethanol, treated with triethylamine (9.60 mL, 68.9 mmol) and heated to reflux. After 5 d, the reaction mixture was concentrated under reduced pressure. The resulting oil was dissolved in CH2Cl2, washed with 2% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a brown oil. Chromatography (SiO2, 5–10% MeOH/CHCl3) gave N,N-dimethyl-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-amine (0.89 g) as a brown oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe resulting oil was dissolved in 75 mL of ethanol
  3. temperatureheated to reflux
  4. waitAfter 5 d
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. dissolutionThe resulting oil was dissolved in CH2Cl2
  7. washwashed with 2% Na2CO3 solution, water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto yield a brown oil

Sources & evidence

ORD record
ord-a7ecb3f1c2cb40caa253ce0b06bf7a34
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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