Acetonitrile → HCID 58964508, compound

HRID 2069283Notes

Reaction equation

HRID 2069283 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][O:11][C:12](=[O:27])[C:13]1[CH:18]=[C:17](F)[C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=1[N+:24]([O-:26])=[O:25].CC#N>O1CCCC1>[CH3:10][O:11][C:12](=[O:27])[C:13]1[CH:18]=[C:17]([N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[O:3])[C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=1[N+:24]([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl esterHCID 178516071HCID 178516071, compound

Product 1

HCID 58964508HCID 58964508, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of NaH (315 mg, 1.4 eq) in 50 ml of tetrahydrofuran, a solution of 2-hydroxypyridine (801 mg, 1.5 eq) in 5 ml of tetrahydrofuran is added drop-wise. The mixture is stirred at room temperature for 30 min before addition of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (1.5 g, 5.61 mmol) in 10 ml of tetrahydrofuran. The resulting mixture is stirred at room temperature for 16 hours. The solvent is removed in vacuo and the crude oil is solubilised in ethyl acetate. The organic phase is washed with sat NaHCO3 solution, dried over sodium sulfate and concentrated in vacuo to afford a crude yellow oil. The crude product is purified by flash-chromatography (ethyl acetate/hexane (0:100 to 100:0)) to obtain 2-nitro-5-(2-oxo-2H-pyridin-1-yl)-4-trifluoromethyl-benzoic acid methyl ester as a yellow solid (1.3 g, 68% yield) (ES-MS: m/z 328 [M+H+CH3CN]+, Rt 4.67 min.).

Workup

  1. customThe solvent is removed in vacuo
  2. washThe organic phase is washed with sat NaHCO3 solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford a crude yellow oil
  6. customThe crude product is purified by flash-chromatography (ethyl acetate/hexane (0:100 to 100:0))

Sources & evidence

ORD record
ord-b0a2d51324b04cffa727b487cd9655ed
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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