Reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[CH:17]=1)([O-:5])=[O:4].I[CH3:19]>CN(C=O)C>[CH3:19][N:15]1[C:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:17][C:10]=2[CH2:11][CH2:12][CH2:13][C:14]1=[O:16]Participants
Procedure
202 mg of NaH (50%) are added to a solution of 771 mg of 7-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in 20 ml of DMF. The reaction medium is stirred for 15 minutes and then 583 mg of iodomethane are added. The mixture is stirred for 4 hours at ambient temperature and then run into ice-cold water and extracted with ethyl acetate. The organic phase is washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a heptane/ethyl acetate (80/20 to 50/50) mixture. 275 mg of 1-methyl-7-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one are obtained in the form of a yellow solid.
Workup
- stirringThe mixture is stirred for 4 hours at ambient temperature
- extractionextracted with ethyl acetate
- washThe organic phase is washed with a saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customPurification
- washis carried out by flash chromatography on silica gel (40-63 μm), elution
Sources & evidence
- ORD record
- ord-0238aa25307e4c28909a2a906207c8a9
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Linked notes
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