Oxalyl chloride → 2-Methyl-5-nitrobenzoyl chloride
Reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][C:8]1C=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:9]=1C(O)=O>CN(C=O)C.C(Cl)Cl>[CH3:7][C:8]1[CH:9]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][C:1]=1[C:2]([Cl:4])=[O:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Oxalyl chloride (0.31 g) was added dropwise to a stirred mixture of 2-methyl-5-nitrobenzoic acid (0.4 g), DMF (a few drops) and methylene chloride (25 ml) which had been cooled to 0° C. The mixture was allowed to warm to ambient temperature and was stirred for five hours. The mixture was evaporated to give 2-methyl-5-nitrobenzoyl chloride which was dissolved in methylene chloride (10 ml) and added dropwise to a stirred mixture of 3-(4-methylpiperazin-1-ylmethyl)aniline (0.44 g), triethylamine (0.49 g) and methylene chloride (10 ml). The mixture was stirred at ambient temperature for 16 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution. The organic phase was evaporated and the residue was purified by column chromatography on an isolute SCX ion exchange column using initially methanol and then a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. There was thus obtained N-[3-(4-methylpiperazin-1-ylmethyl)phenyl]-2-methyl-5-nitrobenzamide(0.46 g); Mass Spectrum: M+H+ 369.
Workup
- temperatureto warm to ambient temperature
- customThe mixture was evaporated
Sources & evidence
- ORD record
- ord-d012cebb1a1c4541ab661d26451db80d
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06794380B2
Reaction notes
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