Anisole → 3-(4-methoxyphenyl)isoquinolin-1(2H)-one

HRID 1251099Notes

Reaction equation

HRID 1251099 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([CH3:11])=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[Li]CCCC.[C:17]1([O:23][CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)=O.CC(C)=O.[Cl-].[NH4+]>C1COCC1.CCOCC>[CH3:24][O:23][C:17]1[CH:22]=[CH:21][C:20]([C:1]2[NH:2][C:3](=[O:4])[C:5]3[C:6]([CH:11]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 7519AnisoleHCID 25517Ammonium ChlorideHCID 75111N-methyl-2-toluamideHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 123280893-(4-methoxyphenyl)isoquinolin-1(2H)-oneYield 24%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of N-methyl-o-toluamide (4.47 g) in THF (100 ml) was added dropwise 1.6 M n-BuLi (40 ml, 2.2 equivalents) in nitrogen atmosphere at 0° C. After stirring for 2 hr, the resulting solution was cooled in a dry ice/acetone bath to −70° C., followed by the addition of anisole (4.0 g) at once. The reaction mixture was drawn out of the dry ice/acetone bath, and then returned to room temperature. Three hours later, an aqueous solution of saturated ammonium chloride and ether were added thereto, which was stirred for further 1 hr. The resulting white precipitates were collected by filtration, and then washed with water, ether and n-hexane, in this order. The resulting precipitates were dried, to give the title compound (1.72 g, yield; 24%).

Workup

  1. customreturned to room temperature
  2. stirringwhich was stirred for further 1 hr
  3. customThe resulting white precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water, ether and n-hexane, in this order
  6. customThe resulting precipitates
  7. customwere dried

Sources & evidence

ORD record
ord-293854a0a4ee4f8e820d20f33d4da078
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

Loading…