Sodium Chloride → (3,4-Dichlorobenzyl)-(8-isopropoxy-2-methylquinolin-4-yl)-amine hydrochloride

HRID 1966530Notes

Reaction equation

HRID 1966530 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH3:18])[CH:8]=1.[H-].[Na+].[CH:25](I)([CH3:27])[CH3:26].[Na+].[Cl-]>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[C:12]([O:17][CH:25]([CH3:27])[CH3:26])[CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH3:18])[CH:8]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 59474753HCID 59474753, compound

Product 1

HCID 68492619(3,4-Dichlorobenzyl)-(8-isopropoxy-2-methylquinolin-4-yl)-amine hydrochlorideYield 34.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3,4-Dichlorobenzylamino)-2-methylquinolin-8-ol (example 41, 70.0 mg, 0.210 mmole) was suspended in dimethylformamide (5 mL) and mixed with sodium hydride (60% in paraffin liq., 9.24 mg). After stirring for 30 min isopropyliodide (37.5 mg, 0.221 mmole) was added dropwise and the mixture was kept under stirring at RT for 16 hrs. Diluted NaCl solution was added and the mixture was extracted with ethyl acetate. The organic phases were dried and concentrated and the residue thus obtained was purified using silica gel chromatography, eluting with dichloromethane:methanol 90:10. Precipitation in Isopropanol/iso-propyl ether/HCl gave a brownish salt (15 mg, 17%). ESI-MS [M+H]+=375.1/379.2 calculated for C20H20Cl2N2O=375 g/mole

Workup

  1. additionwas added dropwise
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic phases were dried
  4. concentrationconcentrated
  5. customthe residue thus obtained
  6. customwas purified
  7. washeluting with dichloromethane:methanol 90:10
  8. customPrecipitation in Isopropanol/iso-propyl ether/HCl

Sources & evidence

ORD record
ord-7b07c2742f874d42a3f80307cdac4bc2
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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