2-Nitrotoluene → N-Hydroxy-2-toluidine

HRID 1383748Notes

Reaction equation

HRID 1383748 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-])=[O:2]>CN1CCOCC1.[Pt]>[C:5]1([CH3:10])[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:1][OH:2]

Participants

4

Reactant 1

HCID 69442-Nitrotoluene

Product 1

HCID 11908N-Hydroxy-2-toluidineYield 82.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 79724-MethylmorpholineSolvent

Procedure

A suspension of 411 g (3 mol) of 2-nitrotoluene and 15 g of platinum on active carbon (F 105 XRS/W 5% from Degussa) in 2.8 l of 4-methylmorpholine was flushed at 0° C. with nitrogen and then with hydrogen. The reaction was carried out at 100 mbar gauge pressure. The reaction was completed after 13 hours. The mixture was flushed with nitrogen and the catalyst was filtered off, after which the solvent was very substantially distilled off at from 45 to 50° C. under reduced pressure. The residue was taken up in 1 l of 1:1 methylene chloride/water and the aqueous phase was acidified with hydrochloric acid and then extracted with methylene chloride. The organic phases were dried and the solvent was distilled off, after which the residue was digested in pentane and the product was filtered off and washed. 305 g of the title compound were obtained as (according to HPLC analysis) 89% strength by weight product.

Workup

  1. customwas flushed at 0° C. with nitrogen
  2. customThe mixture was flushed with nitrogen
  3. filtrationthe catalyst was filtered off
  4. distillationafter which the solvent was very substantially distilled off at from 45 to 50° C. under reduced pressure
  5. extractionextracted with methylene chloride
  6. customThe organic phases were dried
  7. distillationthe solvent was distilled off
  8. filtrationthe product was filtered off
  9. washwashed

Sources & evidence

ORD record
ord-2dc1579496f64890ab54bc0a42af1513
Source dataset
uspto-grants-2001_07
Patent number
US06255489B1

Reaction notes

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