4-Mesyl-2-nitrotoluene → 5-Methanesulfonyl-2-methylaniline

HRID 2390118Notes

Reaction equation

HRID 2390118 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1)(=[O:4])=[O:3]>CCOC(C)=O.[Pt]=O>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][C:7]=1[NH2:12]

Participants

4

Reactant 1

HCID 6871254-Mesyl-2-nitrotoluene

Product 1

HCID 175119545-Methanesulfonyl-2-methylanilineYield 99%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methylsulfonyl-2-nitrotoluene (Alfa; 4.00 g; 18.6 mmol) and platinum oxide (120 mg; 0.53 mmol) in EtOAc (200 mL) was hydrogenated in a PARR apparatus at 5 atm for 75 minutes. The mixture was filtered through a pad of celite and the solvent was evaporated to afford the title compound as a colorless oil (3.41 g, 99%).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-93da97f2895944698e6c26757385b25d
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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