Tetrahydrofuran → HCID 12715767, compound

HRID 711708Notes

Reaction equation

HRID 711708 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-4642c5415b734e1987dfee4b9375683d
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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