5-Nitro-2-(propane-2-sulfonyl)benzonitrile → 5-Amino-2-(isopropylsulfonyl)benzonitrile

HRID 1667610Notes

Reaction equation

HRID 1667610 reaction equation
[CH:1]([S:4]([C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:8]=1[C:9]#[N:10])(=[O:6])=[O:5])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

4

Reactant 1

HCID 574482065-Nitro-2-(propane-2-sulfonyl)benzonitrile

Product 1

HCID 574482075-Amino-2-(isopropylsulfonyl)benzonitrileYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2-(isopropylsulfonyl)-5-nitrobenzonitrile (15B) (1.26 g, 4.96 mmol) in THF (20 mL) was added Pd/C (cat.) and the mixture was hydrogenated at 50 psi overnight. The reaction was filtered to provide 15C (1.09 g). LC-MS: 225.3 (M+H)+.

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe reaction was filtered

Sources & evidence

ORD record
ord-ca001710f8b740baba3b47db7d46c0c7
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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