Dichloromethane → HCID 22935737, compound

HRID 1352499Notes

Reaction equation

HRID 1352499 reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.[C:27](OC(=O)C)(=[O:29])[CH3:28].ClCCl>O1CCOCC1>[C:1]1([N:7]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)[C:27](=[O:29])[CH3:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 5124249N-phenylquinolin-4-amine

Product 1

HCID 22935737HCID 22935737, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of phenyl-quinolin-4-yl-amine (13 g) and N-ethyl-N,N-diisopropylamine (1.5 eq) in dioxane (105 ml) was added acetic anhydride (28.1 ml, 5 eq). The solution was warmed to reflux of dioxane for 5 days. After cooling, dichloromethane was added and the solution was washed by water and sodium hydroxide 1N. The organic layer was separated and dried over sodium sulfate. The solvent was removed and the mixture was purified by chromatography on silica gel (dichloromethane/ethanol (95:5)) to afford N-phenyl-N-quinolin-4-yl-acetamide (10 g).

Workup

  1. temperatureThe solution was warmed
  2. temperatureAfter cooling
  3. washthe solution was washed by water and sodium hydroxide 1N
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed
  7. customthe mixture was purified by chromatography on silica gel (dichloromethane/ethanol (95:5))

Sources & evidence

ORD record
ord-1ae988ca56a24ff9b3665081a3941a4f
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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