N-Iodosuccinimide → HCID 178487750, compound

HRID 1852153Notes

Reaction equation

HRID 1852153 reaction equation
C1C(=O)N([I:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([OH:21])=[N:16][CH:15]=[CH:14]2>CC#N>[I:8][C:14]1[C:13]2[C:18](=[CH:19][CH:20]=[C:11]([O:10][CH3:9])[CH:12]=2)[C:17]([OH:21])=[N:16][CH:15]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178487746HCID 178487746, compound

Product 1

HCID 178487750HCID 178487750, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of NIS (3.31 g, 14.73 mmol) in CH3CN (25 mL) was added 6-methoxyisoquinolin-1-ol (2.58 g, 14.73 mmol). The resulting suspension was slowly warmed to reflux and maintained refluxing for 2 h. After concentration, the residue was taken into water. The solid was collected through filter paper washing with hot water to give a crude product 4-iodo-6-methoxyisoquinolin-1-ol (3.87 g, 87% yield) which was used in the next step with out further purification. MS: MS m/z 302(M++1). 1H NMR (400 MHz, CHLOROFORM-d) δ 16.12 (br. s., 1H), 12.86 (d, J=9.0 Hz, 1H), 12.34 (d, J=5.8 Hz, 1H), 11.89 (dd, J=8.8, 2.5 Hz, 1H), 11.76 (d, J=2.3 Hz, 1H), 8.70-8.62 (m, 3H).

Workup

  1. temperatureThe resulting suspension was slowly warmed
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperaturerefluxing for 2 h
  5. concentrationAfter concentration
  6. customThe solid was collected
  7. filtrationthrough filter paper
  8. washwashing with hot water

Sources & evidence

ORD record
ord-0256e0b65f284aa5b821e7fd5d2a2a4d
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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