Sodium Iodide → 1-Iodo-4-(4-pyridyl-methyl)-phthalazine

HRID 2054194Notes

Reaction equation

HRID 2054194 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[I-:19].[Na+].I>CC(C)=O>[I:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 223864621-Iodo-4-(4-pyridyl-methyl)-phthalazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under exclusion of air, a suspension of 12.8 g (50 mMol) of 1-chloro-4-(4-pyridyl-methyl)-phthalazine (Example 67A.1 in WO 98/35958) and 25 g (166.8 mMol) of sodium-iodide in 0.3 l of acetone is mixed with 20 ml hydroiodic acid (55% Hl in water; 144 mMol) and stirred in the dark during 6 days at RT. Filtration and washing with acetone follow. The remaining solid is suspended in 1 l of water, neutralized with 100 ml of an 1 M Na2CO3 solution, stirred during 10 min, filtered and washed with water, yielding the title compound: An. calc. (C14H10N3I.0.05 H2O) C, 48.31%; H, 2.92%; N, 12.07%; I, 36.46%; H2O, 0.26%; An. meas. C, 48.60%; H, 3.10%; N, 12.08%; I, 36.28%; H2O, 0.28%; FAB-MS (M+H)+=348.

Workup

  1. filtrationFiltration
  2. washwashing with acetone
  3. stirringstirred during 10 min
  4. filtrationfiltered
  5. washwashed with water

Sources & evidence

ORD record
ord-7e6954878843402f8b90a75dddd2ea7b
Source dataset
uspto-grants-2008_02
Patent number
US07329660B2

Reaction notes

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