Ethoxyacetyl chloride → HCID 67051012, compound

HRID 598314Notes

Reaction equation

HRID 598314 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][C:20]([NH2:26])=[C:19]2[NH:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH2:8]([O:15][C:16]1[CH:25]=[CH:24][C:23]2[N:22]=[CH:21][C:20]3[N:26]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:27]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:19]=3[C:18]=2[CH:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 67050972HCID 67050972, compound

Product 1

HCID 67051012HCID 67051012, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethoxyacetyl chloride (3.81 g, 31.1 mmol) was slowly added to a chilled solution of 6-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine (9.1 g, 28.3 mmol) in pyridine (60 mL). The reaction was allowed to warm to ambient temperature and then heated at reflux for three hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (200 mL). The resulting solution was washed with water (3×100 mL) and concentrated under reduced pressure. The concentrated solution was passed through a layer of silica gel (eluting with dichloromethane:methanol 95:5) and concentrated under reduced pressure to provide 3.6 g of 8-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane (200 mL)
  5. washThe resulting solution was washed with water (3×100 mL)
  6. concentrationconcentrated under reduced pressure
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35d874c59e8d492aaeea46ba244f0fce
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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