Iodide Ion → HCID 67339253, compound

HRID 2092348Notes

Reaction equation

HRID 2092348 reaction equation
N[C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[N:5][NH:6][C:7]2=[O:13].N([O-])=O.[Na+].[I-:18]>Cl.O>[I:18][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[N:5][NH:6][C:7]2=[O:13]

Participants

6

Reactant 3

HCID 30165Iodide IonHCID 23668193Sodium NitriteHCID 67340581HCID 67340581, compound

Product 1

HCID 67339253HCID 67339253, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5-amino-6-methylphthalazin-1(2H)-one (7.57 g, 43 mmol) in conc. aqueous HCl (250 ml) charged to a 500 mL round bottom, sodium nitrite (3.6 g, 52 mmol) in 50 mL water was added at 0° C. The mixture was then allowed to stir for 90 min at that temperature. Then, KI (22 g, 130 mmol) in water (50 ml) was added. The reaction mixture was stirred at 70° C. for 2 hrs, forming a dark precipitate on initial addition of iodide. Upon cooling to ambient temperature, the dark ppt was collected by filtration and stirred in a solution of saturated sodium sulfite, forming a light yellow precipitate. This precipitate was collected by filtration and washed with excess water. The light yellow solid was dried in a vacuum oven overnight to give 5-iodo-6-methylphthalazin-1(2H)-one (8.5 g, 69% yield. MS (M+H)+ 287.

Workup

  1. stirringThe reaction mixture was stirred at 70° C. for 2 hrs
  2. customforming a dark precipitate on initial
  3. filtrationthe dark ppt was collected by filtration
  4. stirringstirred in a solution of saturated sodium sulfite
  5. customforming a light yellow precipitate
  6. filtrationThis precipitate was collected by filtration
  7. washwashed with excess water
  8. customThe light yellow solid was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-29128139440b4d5285c74b4c96bd4ea8
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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