Iodine → 7-Methylisoquinolin-1(2H)-one
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureis heated
- temperatureThe mixture is cooled to room temperature
- concentrationthen concentrated to dryness
- customThe residue is purified by column chromatography
- 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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