1-(Methanesulfonylmethyl)-4-nitrobenzene → 4-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)

HRID 2281470Notes

Reaction equation

[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C([O-])=O.[NH4+]>CCO.O.CCOC(C)=O.[Fe]>[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 1-(methylsulfonylmethyl)-4-nitrobenzene (1.5 g, 7 mmol) in EtOH (20 mL) and H2O (10 mL) was added iron (1.96 g, 35 mmol) and ammonium formate (4.41 g, 70 mmol). After heating at 90° C. for 2 h, it was diluted with EtOAc, washed with saturated NaHCO3, brine, dried and concentrated to give 4-(methylsulfonylmethyl)aniline (0.5 g).

Workup

washwashed with saturated NaHCO3, brine
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-1ce7afb072eb4fe5b371153f5ef15e04
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139581B2

Reaction notes

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