Dichloromethane → Methyl 3-methoxyiminomethyl-4-nitrobenzoate
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7])=O.C(Cl)Cl.Cl.[O:20]([NH2:22])[CH3:21].C([O-])(=O)C.[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C.O>[CH3:21][O:20][N:22]=[CH:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a well stirred mixture of 195 g of methyl 3-formyl-4-nitrobenzoate, 1 l methylene chloride and 370 mL of water was added sequentially 77.6 g of methoxylamine hydrochloride, 76.2 g of sodium acetate and 6.8 g of tetra-n-butylammonium hydrogen sulfate. The resulting mixture was stirred overnight at room temperature, then diluted with 2 l of ethyl ether. The organic phase was separated and washed sequentially with water (1×500 mL), 2% aqueous hydrochloric acid (2×500 mL), water (2×250 mL), and brine (1×250 mL); then dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator yielding 218.6 g of the expected methyl 3-methoxyiminomethyl-4-nitrobenzoate as a reddish oil that solidified upon standing, and which was used as such in the next step.
Workup
- stirringThe resulting mixture was stirred overnight at room temperature
- customThe organic phase was separated
- washwashed sequentially with water (1×500 mL), 2% aqueous hydrochloric acid (2×500 mL), water (2×250 mL), and brine (1×250 mL)
- dry with materialthen dried over anhydrous magnesium sulfate
- customThe solvent was removed
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-187f9e34179f49dcb2d59c71a47963b6
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107316
Reaction notes
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