Methyl iodide → (cis)-4-(3,4-Dimethoxyphenyl)-2-methyl-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C@H:22]3[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[C:16](=[O:23])[NH:15][N:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].I[CH3:25]>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C@H:22]3[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[C:16](=[O:23])[N:15]([CH3:25])[N:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
6 mmol of a 60% suspension of sodium hydride in mineral oil was added to a suspension of 5 mmol of compound 1 in about 40 ml of dimethylformamide, under a flow of nitrogen at room temperature. After stirring this mixture for 30 minutes, 7 mmol of iodomethane was added and the resulting mixture was stirred for another 4 hours, after which the solvent was evaporated. The residue was partitioned between ethyl acetate and water, the organic layer was dried over magnesium sulfate and evaporated. The residue was purified by chromatography (dichloromethane). Crystallized from petroleum ether (60-95° C.). M.p. 110-112° C.
Workup
- stirringthe resulting mixture was stirred for another 4 hours
- customafter which the solvent was evaporated
- customThe residue was partitioned between ethyl acetate and water
- dry with materialthe organic layer was dried over magnesium sulfate
- customevaporated
- customThe residue was purified by chromatography (dichloromethane)
- customCrystallized from petroleum ether (60-95° C.)
Sources & evidence
- ORD record
- ord-1e050df5a8f64e808385a028b55c4ce4
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06103718
Reaction notes
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