Iodine → 7-Methylisoquinolin-1(2H)-one

HRID 651588Notes

Reaction equation

HRID 651588 reaction equation
II.[N:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=[C:4]=[O:5]>ClC1C=CC=CC=1Cl>[CH3:14][C:11]1[CH:10]=[C:9]2[C:8]([CH:7]=[CH:6][NH:3][C:4]2=[O:5])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 807IodineHCID 545437911-(2-Isocyanato-vinyl)-4-methyl-benzene

Product 1

HCID 156938767-Methylisoquinolin-1(2H)-oneYield 31.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

Iodine (0.63 g, 2.51 mmol) is added to a solution of 1-(2-isocyanato-vinyl)-4-methyl-benzene (ca. 20 g, 125.6 mmol) in o-dichlorobenzene (125 mL), then is heated to reflux (180° C.) overnight. The mixture is cooled to room temperature then concentrated to dryness. The residue is purified by column chromatography eluting with 40% EtOAc/hexanes. The product (6.23 g, 39.1 mmol) is obtained as a tan solid.

Workup

  1. temperatureis heated
  2. temperatureThe mixture is cooled to room temperature
  3. concentrationthen concentrated to dryness
  4. customThe residue is purified by column chromatography
  5. washeluting with 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-551e278571664f97bbdf9be893b956d7
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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