Dichloromethane → HCID 86643434, compound

HRID 1500550Notes

Reaction equation

HRID 1500550 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].ClCCl.[OH:9][CH2:10][CH:11]([CH3:26])[CH2:12][CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][C:21](=[O:25])[NH:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>O>[CH3:26][CH:11]([CH2:12][CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][C:21](=[O:25])[NH:22]2)=[CH:17][CH:16]=1)[CH2:10][O:9][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66884704HCID 66884704, compound

Product 1

HCID 86643434HCID 86643434, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (1.0 ml) was added to a dichloromethane (80 ml) solution of 2.8 g of 7-(4-hydroxy-3-methyl butoxy)-3,4-dihydro-1H-quinolin-2-one and 2.4 ml of triethylamine while being stirred under ice-cooling and stirred at room temperature overnight. Water was added to the reaction solution, which was then extracted with dichloromethane and, after washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1), and methanesulfonic acid 2-methyl-4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yloxy)butyl ester (2.8 g) was obtained in the form of a green powder.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature overnight
  3. extractionwas then extracted with dichloromethane
  4. washafter washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-9f0016a1213d47539b74caa54122f71d
Source dataset
uspto-grants-2015_12
Patent number
US09206167B2

Reaction notes

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