Nitric Acid → HCID 21696676, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[N+:4]([O-])[C:3]=1[C:10]([O:12]C)=[O:11].OS(O)(=O)=O.O=S(=O)=O.[N+:23]([O-])([OH:25])=[O:24].C(=O)(O)[O-].[Na+]>OS(O)(=O)=O.C(OCC)(=O)C>[N+:23]([C:7]1[CH:6]=[C:5]([Cl:8])[N:4]=[C:3]([C:10]([OH:12])=[O:11])[C:2]=1[Cl:1])([O-:25])=[O:24]Participants
7
Conditions
- Temperature
- 65 °C
Procedure
Methyl 3,6-dichloropyridine-2-carboxylate N-oxide (5.0 g, 22.52 mmol) was dissolved in a minimum amount of H2SO4. The mixture was cooled in an ice/water bath and to it was slowly added 30% oleum (9.6 mL) and fuming HNO3 (9.6 mL), gradually heated to 65° C. and stirred for 48 hr. The cooled reaction mixture was diluted with ethyl acetate (200 mL) and to it was carefully added saturated sodium bicarbonate. The product was extracted with ethyl acetate (2×150 mL) and the combined extracts were dried (MgSO4) and concentrated to give 0.10 g of a yellow solid; mp 192-193° C.
Workup
- temperatureThe mixture was cooled in an ice/water bath and to it
- customThe cooled reaction mixture
- extractionThe product was extracted with ethyl acetate (2×150 mL)
- dry with materialthe combined extracts were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b7278315d1144850911926697803a758
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297197B1
Reaction notes
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