N-Iodosuccinimide → 5-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one

HRID 577600Notes

Reaction equation

HRID 577600 reaction equation
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:19]=[C:18]([C:20]2[N:24]([CH3:25])[N:23]=[N:22][C:21]=2[CH3:26])[CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][NH:14][C:15]2=[O:27].ClCCl.CO>C(O)(=O)C>[NH2:9][C:10]1[C:19]([I:1])=[C:18]([C:20]2[N:24]([CH3:25])[N:23]=[N:22][C:21]=2[CH3:26])[CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][NH:14][C:15]2=[O:27]

Participants

5

Reactant 3

HCID 120273N-Iodosuccinimide2×HCID 21226129Dichloromethane methanolHCID 867238265-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 867238275-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-oneYield 61.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-iodosuccinimide (5.27 g, 23.43 mmol) was added in portions to a solution of 5-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (293d, 5.5 g, 21.3 mmol) in glacial acetic acid (400 mL) and the resulting mixture stirred at room temperature for three days. A second portion of N-iodosuccinimide (2.6 g, 12.7 mmol) was then added and stirring continued at room temperature overnight. The mixture was concentrated under vacuum to remove acetic acid. The residue was dissolved in methanol (200 mL), concentrated to dryness, and purified by silica gel chromatography (eluting with 1:1 to 1:2 petroleum ether/ethyl acetate and then with 100:1 to 50:1 dichloromethane/methanol), to give 5-amino-7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-6-iodo-3,4-dihydroisoquinolin-1(2H)-one (293e, 5.0 g, 60% yield) as a yellow solid.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature overnight
  3. concentrationThe mixture was concentrated under vacuum
  4. customto remove acetic acid
  5. dissolutionThe residue was dissolved in methanol (200 mL)
  6. concentrationconcentrated to dryness
  7. custompurified by silica gel chromatography (
  8. washeluting with 1:1 to 1:2 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-80270a9b40f042a1a5c64b8df6d0f747
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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