1-[(Methylsulfanyl)methyl]-2-nitrobenzene → 2-[(Methylsulfanyl)methyl]aniline

HRID 2295385Notes

Reaction equation

HRID 2295385 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-])=O>C(O)(=O)C.C(O)C.[Fe]>[CH3:1][S:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10]

Participants

5

Reactant 1

HCID 130574171-[(Methylsulfanyl)methyl]-2-nitrobenzene

Product 1

HCID 123574872-[(Methylsulfanyl)methyl]aniline

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Iron powder (60 g, 1.0 g-atom) was added slowly through a solid addition funnel to a solution of 53.5 g (0.29 mol) of o-methylthiomethylnitrobenzene in 210 ml of glacial acetic acid and 600 ml of absolute ethanol under reflux over a period of 45 minutes. The mixture was then refluxed for 3 hours. The iron powder was filtered off and the filtrate was diluted with 800 ml of water. The aqueous mixture was extracted twice with 200 ml ethyl acetate and twice with 200 ml ether. The combined organic extracts were washed with water, dried and concentrated to yield 48 g (75% pure) of orange oil.

Workup

  1. temperatureunder reflux over a period of 45 minutes
  2. temperatureThe mixture was then refluxed for 3 hours
  3. filtrationThe iron powder was filtered off
  4. additionthe filtrate was diluted with 800 ml of water
  5. extractionThe aqueous mixture was extracted twice with 200 ml ethyl acetate and twice with 200 ml ether
  6. washThe combined organic extracts were washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto yield 48 g (75% pure) of orange oil

Sources & evidence

ORD record
ord-47a5708a8e7b446695bd4633ddd1c78a
Source dataset
uspto-grants-1984_01
Patent number
US04424377

Reaction notes

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