Sodium Carbonate → 3-(2-Fluoro-ethoxy)-8-nitro-quinoline

HRID 593349Notes

Reaction equation

HRID 593349 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][C:10]([OH:14])=[CH:9]2)([O-:3])=[O:2].[F:15][CH:16](F)[CH2:17]OS(C)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.ClCCl>[F:15][CH2:16][CH2:17][O:14][C:10]1[CH:11]=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 543669748-Nitro-3-quinolinolHCID 567764922,2-Difluoroethyl methanesulfonate

Product 1

HCID 866679923-(2-Fluoro-ethoxy)-8-nitro-quinolineYield 24.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 8-nitro-quinolin-3-ol (500 mg, 2.63 mmol), methanesulphonic acid 2,2-difluoro-ethyl ester (463 mg, 2.9 mmol), ad potassium carbonate (810 mg, 5.86 mmol) in dimethylformamide (7 ml) was heated at 100° C. for 16 hours. For the workup, the reaction mixture was cooled to room temperature, then saturated aqueous sodium carbonate solution and dichloromethane were added. The organic layer was separated, dried over sodium sulphate, then evaporated. The crude product was purified by chromatography on silica gel using a gradient of cyclohexane/ethyl acetate=10:1 to 1:1 as the eluent yielding 150 mg (24%) of the 3-(2-fluoro-ethoxy)-8-nitro-quinoline as a yellow solid; (calculated) C11H9FN2O3 [236.2]; (found) [M+H]+=237.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe crude product was purified by chromatography on silica gel using a gradient of cyclohexane/ethyl acetate=10:1 to 1:1 as the eluent

Sources & evidence

ORD record
ord-5f7590d772184e05bdf7dd353a7208c4
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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