Hydrochloric Acid → HCID 15289704, compound
Reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-])=O)=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)[N:3]=1.Cl>C(O)C>[NH2:18][C:5]1[C:4]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)=[N:3][C:2]([Cl:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
In 20ml of ethanol were suspended 0.91 g of 2-chloro-3,4-diethoxycarbonyl-5-nitro-6-(4-nitrophenyl)pyridine and 1.11 g of reduced iron, and the suspension was heated to 60° C. After 4.7 ml of conc. hydrochloric acid was added, the mixture was heated under reflux for 20 minutes. After the reaction mixture was concentrated, extraction with ethyl acetate was conducted. The extract was washed with an aqueous solution of sodium hydrogencarbonate and an aqueous solution of sodium chloride consecutively, and dried over magnesium sulfate. After concentration, the residue was subjected to silica gel column chromatography (eluent:chloroform/methanol 40:1), to give 0.58 g of the title compound as yellow prisms.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 20 minutes
- concentrationAfter the reaction mixture was concentrated
- extractionextraction with ethyl acetate
- washThe extract was washed with an aqueous solution of sodium hydrogencarbonate
- dry with materialan aqueous solution of sodium chloride consecutively, and dried over magnesium sulfate
- concentrationAfter concentration
Sources & evidence
- ORD record
- ord-91843e65723d453dac6deaa963309439
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420275
Reaction notes
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