Hydrochloric Acid → HCID 59216594, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH3:13])([O-:3])=[O:2].[CH2:14]([O:16][C:17](=[O:23])[C:18](OCC)=[O:19])[CH3:15].CC[O-].[Na+].Cl>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][C:18](=[O:19])[C:17]([O:16][CH2:14][CH3:15])=[O:23])([O-:3])=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
2,6-Dinitrotoluene (10.0 g, 54.9 mmol) and oxalic acid diethylester (16.1 g, 110 mmol) are dissolved in ethanol (100 ml). Sodium ethylate (apx 2.5 N in ethanol, 54.9 mmol) is added, the mixture is stirred at 40° C. for 2 h. The solution is cooled to room temperature, adjusted to pH=3-4 with 2N hydrochloric acid, the solvent is evaporated in vacuo, the residue is partitioned between ethyl acetate and water, the organic layer is washed with water twice, dried over magnesium sulfate, filtered and evaporated. The crude product is purified with column chromatography on silica gel (eluent: cyclohexane/ethyl acetate, 2:1). Yield: 3.15 g (20%), mixture of keto/enol tautomers
Workup
- temperatureThe solution is cooled to room temperature
- customthe solvent is evaporated in vacuo
- customthe residue is partitioned between ethyl acetate and water
- washthe organic layer is washed with water twice
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe crude product is purified with column chromatography on silica gel (eluent: cyclohexane/ethyl acetate, 2:1)
- additionYield: 3.15 g (20%), mixture of keto/enol tautomers
Sources & evidence
- ORD record
- ord-36d0a6bcace249a3969b511e3fb086cf
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683076B2
Reaction notes
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