Water → HCID 19603298, compound

HRID 1604602Notes

Reaction equation

HRID 1604602 reaction equation
C([O:4][CH2:5][C:6]([N:8]([C:10]1[C:11]([Cl:30])=[C:12]([C:26]([Cl:29])=[CH:27][CH:28]=1)[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[C:22]([CH3:25])[CH:21]=[CH:20]2)[CH3:9])=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl.O>CO>[Cl:30][C:11]1[C:10]([N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH3:9])=[CH:28][CH:27]=[C:26]([Cl:29])[C:12]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[C:22]([CH3:25])[CH:21]=[CH:20]2

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 11430Potassium CarbonateHCID 19603239HCID 19603239, compound

Product 1

HCID 19603298HCID 19603298, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-[3-(N-acetoxyacetyl-n-methylamino)-2,6-dichlorobenzyloxy]-2-methylquinoline (640 mg) in methanol (6.4 ml) was added potassium carbonate (395 mg), and the mixture was stireed for 2 hours at ambient temperature. To the mixture was added chloroform and water, the organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (chloroform:ethyl acetate=3.1, V/V) to give 8-[2,6-dichloro-3-(N-hydroxyacetyl-N-methylamino)benzyloxy]-2-methylquinoline (580 mg) as colorless amorphous.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (chloroform:ethyl acetate=3.1, V/V)

Sources & evidence

ORD record
ord-55ab4c1bd2144bef8df99add04a6a2dd
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

Loading…