Sodium Iodide → HCID 87940286, compound

HRID 2211813Notes

Reaction equation

HRID 2211813 reaction equation
[OH-].[Na+:2].[Na+].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.Cl[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH3:27])[CH:18]=1.[I-].[Na+]>C(O)C>[Na+:2].[CH3:27][C:19]1[CH:18]=[C:17]([CH2:16][O:4][C:5]2[CH:10]=[CH:9][C:8]([S:11]([O-:14])(=[O:12])=[O:13])=[CH:7][CH:6]=2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 4379756Sodium 4-hydroxybenzenesulfonateHCID 115357194-(Chloromethyl)-2-methylquinoline

Product 1

HCID 87940286HCID 87940286, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide 3.0 M (8.7 ml) was added to a suspension of 4-hydroxybezenesulfonic acid sodium salt (5.0 g, 22.0 mmol), 4-chloromethyl-2-methylquinoline (5.0 g, 26.0 mmol) and sodium iodide (0.4 g, 2.7 mmol) in ethanol (80 ml). The reaction was heated to reflux for 18 h, allowed to cool to room temperature to crystallize a white solid. The solids were filtered off, washed with ethanol, chloroform and dried in vacuo to give 4-[(2-methyl-4-quinolinyl)methoxy]benzenesulfonic acid sodium salt (5.5 g, 73%) as a crystalline solid. MS found: (M−Na)−=328.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 18 h
  3. customto crystallize a white solid
  4. filtrationThe solids were filtered off
  5. washwashed with ethanol, chloroform
  6. customdried in vacuo

Sources & evidence

ORD record
ord-29776324be6341ba930db63c57b13995
Source dataset
uspto-grants-2006_09
Patent number
US07101883B2

Reaction notes

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