Potassium Hydroxide → HCID 21824655, compound

HRID 1968740Notes

Reaction equation

HRID 1968740 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7][C:6]=2[C:5]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:4][CH:3]=1.[OH-].[K+].[Cl:19][O-].[Na+]>O>[Cl:19][C:3]1[CH:4]=[C:5]([S:13]([OH:16])(=[O:15])=[O:14])[C:6]2[CH:7]=[CH:8][C:9]([CH3:12])=[N:10][C:11]=2[C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 17122768-hydroxy-2-methyl-quinoline-5-sulfonic AcidHCID 23665760Sodium Hypochlorite

Product 1

HCID 21824655HCID 21824655, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-Hydroxy-2-methyl-quinoline-5-sulfonic acid (14.0 g, 58.52 mmol) was added to a solution of potassium hydroxide (9.20 g, 164 mmol, 2.8 equiv) in water (136 ml) to form a yellow solution. An aqueous solution of sodium hypochlorite (13%, 136 ml) was added. The mixture was stirred at room temperature for 90 minutes. Upon dilution with water (300 ml), the mixture was filtered through amberlite IR-120 (H+). After washing the column with water (2 liters), the eluent was concentrated (to ˜200 ml) and diluted with acetone (300 ml). The precipitate was filtered off and washed with acetone to afford the title compound (5.51 g, 34%). 1H NMR (400 MHz, d6-DMSO): δ=8.52 (d, J=8.3 Hz, 1H), 7.67 (d, J=8.3 Hz, 1H), 7.00 (s, 1H), 2.58 (s, 3H). MS (ES−): 274 (M−H)−.

Workup

  1. customto form a yellow solution
  2. filtrationUpon dilution with water (300 ml), the mixture was filtered through amberlite IR-120 (H+)
  3. washAfter washing the column with water (2 liters)
  4. concentrationthe eluent was concentrated (to ˜200 ml)
  5. additiondiluted with acetone (300 ml)
  6. filtrationThe precipitate was filtered off
  7. washwashed with acetone

Sources & evidence

ORD record
ord-e5b9df65fd464b49bea4816626dba80d
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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