Tetrahydrofuran → HCID 12715767, compound

HRID 471571Notes

Reaction equation

HRID 471571 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:4]=1[C:5]#[N:6].C1COCC1.CCOC(C)=O>CCO.[Pd]>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:3]([S:2][CH3:1])[C:4]=1[C:5]#[N:6]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 12715768HCID 12715768, compound

Product 1

HCID 12715767HCID 12715767, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(methylthio)-6-nitrobenzonitrile (Example 104c) (1.5 g, 7.73 mmol) in EtOH (150 ml)/THF (50 ml)/EtOAc (50 ml) was added 200 mg of 10% Pd/C. The reaction mixture was hydrogenated on part shaker overnight. After the filtration, the filtered solution was dried down under vacuum, and the residue was purified by chromatography on silica gel eluting with EtOAc/Hexane to give the title compound (79%). 1H NMR (400 MHz, CDCl3) δ 2.51 (s, 3H), 4.47 (s, 2H), 6.53-6.51 (m, 1H), 6.58 (d, J=8.0 Hz, 1H), 7.27-7.21 (m, 1H).

Workup

  1. filtrationAfter the filtration
  2. customthe filtered solution was dried down under vacuum
  3. customthe residue was purified by chromatography on silica gel eluting with EtOAc/Hexane

Sources & evidence

ORD record
ord-11e73d900d8b40ac94751615a72b0f91
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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