Benzene → HCID 22401378, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([CH2:14]C(O)=O)=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C1C=CC=CC=1.C([N:49]([CH2:52]C)CC)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([CH2:14][N:49]=[C:52]=[O:31])=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
Procedure
To a mixture of 6-chloro-1,2-dihydro-2-methyl-1-oxo-4-phenyl-3-isoquinoline acetic acid (Reference Example 9 Step 2) (330 mg), diphenylphosphoryl azide (0.29 ml) and benzene (20 ml) was added dropwise triethylamine (0.14 ml) while stirring at room temperature. This mixture was stirred for one hour at room temperature, then for 30 minutes by heating under reflux {in the reaction mixture, (6-chloro-1,2-dihydro-2-methyl-1-oxo-4-phenylisoquinolin-3-yl)methyl isocyanate was produced}, to which was then added 3-isopropoxyaniline (180 mg). The mixture was heated for 30 minutes under reflux. The solvent was distilled off. To the residue was added ethyl acetate. This mixture was washed with water, dilute hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate and water, successively, which was dried (Na2SO4), followed by distilling off the solvent to give the title compound as colorless crystals (390 mg). The physico-chemical data of this product were in agreement with those of the compound obtained in Method A.
Workup
- stirringThis mixture was stirred for one hour at room temperature
- temperaturefor 30 minutes by heating
- temperatureunder reflux {in the reaction mixture
Sources & evidence
- ORD record
- ord-a0a8f704bccd462d9ec1f74ed2894d57
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05527811
Reaction notes
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