Pyridine → 4-Nitro-2-(2',2',2'-trichloroethoxycarbonylamino)benzoic Acid
Reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[N+:10]([C:13]1[CH:14]=[C:15]([NH2:22])[C:16](=[CH:20][CH:21]=1)[C:17]([OH:19])=[O:18])([O-:12])=[O:11].N1C=CC=CC=1>ClCCl>[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:22][C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[CH:14]=1)([O-:12])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2,2,2-trichloroethylchloroformate (Troc—Cl) (1.66 mL, 12.1 mmol) in dry dichloromethane (25 mL) was added drop wise to a solution of 4-nitroanthranilic acid 144 (2 g, 11 mmol) and pyridine (1.78 mL, 22 mmol) in dichloromethane (25 ml) at 0° C. The solution was allowed to stir at 25° C. for 5 hours. The reaction mixture was washed with dilute HCl (1N, 2×50 mL), water (1×50 mL), brine (1×2 5 mL) and dried over MgSO4. Removal of excess solvent by rotary evaporation under reduced pressure afforded the crude product which was used in the subsequent reaction without further purification.
Workup
- washThe reaction mixture was washed with dilute HCl (1N, 2×50 mL), water (1×50 mL), brine (1×2 5 mL)
- dry with materialdried over MgSO4
- customRemoval of excess solvent
- customby rotary evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-c133cdb0bef8414dac5dba06441f555d
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07049311B1
Reaction notes
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