Trifluoroacetic anhydride → HCID 11252660, compound
Reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:16]>C(#N)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N+:3]=1[O-:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Urea hydroperoxid complex (1.19 g, 12.6 mmol) was added to a stirred solution of ethyl 6-chloronicotinate (1.10 g, 6.0 mmol) in acetonitrile (15 mL) at room temperature. This mixture was stirred for 10 min at 0° C. followed by slow addition of an acetonitrile solution (5 mL) of trifluoroacetic anhydride (2.52 g, 12.0 mmol). After the addition the mixture was stirred for 2 h at room temperature. Thereafter, the reaction mixture was diluted with a saturated aqueous NaHCO3 solution and extracted with dichloromethane. The organic phase was dried (Na2SO4) and concentrated to afford 0.98 g (81% yield) of the title compound as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 8.94 (s, 1H), 7.81 (dd, J=8.4, 1.6 Hz, 1H), 7.60 (d, J=8.4 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 1.40 (t, J=7.2 Hz, 3H); MS (EI) m/z 202 and 204 (M++1).
Workup
- additionAfter the addition the mixture
- stirringwas stirred for 2 h at room temperature
- extractionextracted with dichloromethane
- dry with materialThe organic phase was dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6dc78e9ec6cc4549bb9120610bd7fa1a
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683067B2
Reaction notes
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