Sodium Hydroxide → HCID 19087788, compound

HRID 1464376Notes

Reaction equation

HRID 1464376 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6](O)[CH:7]=1.[OH-:14].[Na+].Cl[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1>CN(C=O)C.CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[O:14][CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 203942-(Chloromethyl)quinolineHCID 18786341HCID 18786341, compound

Product 1

HCID 19087788HCID 19087788, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

18.4 g (0.1 mol) of the compound from Example I are dissolved in 50 ml of DMF and 4 g (0.1 mol) of NaOH in 40 ml of methanol are added. 17.8 g (0.1 mol) of 2-chloromethylquinoline in 50 ml of DMF are added dropwise to this mixture with stirring and it is then heated at 100° C. for 5 h. After cooling, the solvent is evaporated in vacuo, the residue is taken up in dichloromethane, and the solution is washed twice with water, dried and concentrated in vacuo to a small volume. Separation is carried out by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=9:1 to 8:2).

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated in vacuo
  3. washthe solution is washed twice with water
  4. customdried
  5. concentrationconcentrated in vacuo to a small volume
  6. customSeparation

Sources & evidence

ORD record
ord-ee2cef3ccbaa41b7bdd7f6362a504bd2
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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