Trifluoromethanesulfonic anhydride → HCID 11016069, compound

HRID 1241700Notes

Reaction equation

HRID 1241700 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]2=[N:23][C:24]3[C:37]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[N:31]([CH3:38])[C:30]4[C:25]=3[C:26]([CH:27]=[C:28](O)[CH:29]=4)=[C:19]2[CH:18]=1>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]2=[N:23][C:24]3[C:37]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[N:31]([CH3:38])[C:30]4[C:25]=3[C:26]([CH:27]=[C:28]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:29]=4)=[C:19]2[CH:18]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 178479874HCID 178479874, compound2×

Product 1

HCID 11016069HCID 11016069, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Method L) Under an atmosphere of nitrogen, trifluoromethanesulphonic acid anhydride (1.14 ml, 6.4 mmol, 1 eq) was added dropwise to a stirred cold (0° C.) suspension of 3-chloro-6-hydroxy-8-methyl-8H-quino[4,3,2-kl]acridine, 36 (2.23 g, 6.4 mmol) in DCM (1 L). On warming to RT a green solution was formed. Aqueous work-up (water, 500 mL), separation of the organic layer, drying (MgSO4), filtering, adsorption onto silica, and column chromatography (85:15 hexane:ethyl acetate) gave the title compound as a yellow solid, (2 g, 4.3 mmol, 67%).

Workup

  1. customwas formed
  2. customAqueous work-up (water, 500 mL), separation of the organic layer
  3. dry with materialdrying (MgSO4)
  4. filtrationfiltering, adsorption onto silica, and column chromatography (85:15 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-793d12fb630242be98f1e75c71b3c819
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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