Trifluoromethanesulfonic anhydride → HCID 54023713, compound
Reaction equation
C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[F:23][C:24]([F:37])([F:36])[S:25]([O:28]S(C(F)(F)F)(=O)=O)(=[O:27])=[O:26].[Cl:38][C:39]1[CH:48]=[C:47]2[C:42]([C:43](O)=[C:44]([C:50]3[CH:55]=[C:54]([CH3:56])[CH:53]=[C:52]([CH3:57])[CH:51]=3)[C:45](=[O:49])[NH:46]2)=[CH:41][C:40]=1[N+:59]([O-:61])=[O:60]>>[Cl:38][C:39]1[CH:48]=[C:47]2[C:42]([C:43]([O:28][S:25]([C:24]([F:37])([F:36])[F:23])(=[O:27])=[O:26])=[C:44]([C:50]3[CH:55]=[C:54]([CH3:56])[CH:53]=[C:52]([CH3:57])[CH:51]=3)[C:45](=[O:49])[NH:46]2)=[CH:41][C:40]=1[N+:59]([O-:61])=[O:60]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (1.0 g in 50 mL dry methylene chloride) was added 0.455 ml diazabicycloundecene and the mixture cooled to -78° C. To this was added trifluoromethanesulfonic anhydride (0.51 mL) dropwise via syringe and the mixture stirred at low temperature. After 1 hour, the reaction was quenched by the addition of saturated ammonium chloride (35 mL) and extracted with ethyl acetate (3×75 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2) gave the title compound (629 mg).
Workup
- customthe reaction was quenched by the addition of saturated ammonium chloride (35 mL)
- extractionextracted with ethyl acetate (3×75 mL)
- washThe organics were washed with water (50 mL) and brine (50 mL)
- dry with materialthen dried over magnesium sulfate
- customPurification of the
- concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2)
Sources & evidence
- ORD record
- ord-59911d1c1743434daa7684f1673764f6
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147088
Reaction notes
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