Potassium Acetate → 2,2,2-Trifluoro-1-(4-hydroxy-5-nitro-10-aza-tricyclo(6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone

HRID 10095Notes

Reaction equation

HRID 10095 reaction equation
[N+:1]([C:4]1[C:14]([N+]([O-])=O)=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])(=[O:27])C.[K+]>CS(C)=O.O>[F:21][C:20]([F:23])([F:22])[C:19]([N:9]1[CH2:10][CH:11]2[CH2:18][CH:7]([C:6]3[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:14]([OH:27])=[CH:13][C:12]=32)[CH2:8]1)=[O:24]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 218647441-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 218647282,2,2-Trifluoro-1-(4-hydroxy-5-nitro-10-aza-tricyclo(6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanoneYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (900 mg, 2.61 mmol) and potassium acetate (KOAc) (2.6 g, 26.1 mmol) were dissolved in DMSO (10 mL) and warmed with stirring to 100° C. for 16 hours. The mixture was cooled and diluted with H2O (50 mL) then extracted with 80% ethyl acetate/hexanes (6×25 mL). The organic layer was washed with H2O (3×20 mL), dried (Na2SO4), filtered and concentrated and purified by chromatography to give an oil (575 mg, 70%). (TLC 50% ethyl acetate/hexanes (NH3) Rf 0.56)

Workup

  1. temperaturewarmed
  2. temperatureThe mixture was cooled
  3. extractionthen extracted with 80% ethyl acetate/hexanes (6×25 mL)
  4. washThe organic layer was washed with H2O (3×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-c332f48e15544b4e8f7002466853992f
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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