5-Bromo-1-methoxy-2-methyl-3-nitrobenzene → 5-Bromo-3-methoxy-2-methylaniline

HRID 1889252Notes

Reaction equation

HRID 1889252 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1>[Fe].C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([CH3:11])=[C:6]([CH:7]=1)[NH2:8]

Participants

4

Reactant 1

HCID 247281025-Bromo-1-methoxy-2-methyl-3-nitrobenzene

Product 1

HCID 272747255-Bromo-3-methoxy-2-methylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A heterogeneous reaction mixture of 4-bromo-2-methoxy-6-nitrotoluene (500 mg, 2.032 mmol), acetic acid (20 ml), and iron (1135 mg, 20.32 mmol) was stirred at rt for 24 hr. Ethyl actetate was added, then the mixture was filtered through celite and the filtrate concentrated. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with further ethyl acetate. The combined organic phases were washed with water and brine, then dried over sodium sulfate, filtered and concentrated to afford the title compound. MS m/z: 218.0 (M+H)+.

Workup

  1. additionEthyl actetate was added
  2. filtrationthe mixture was filtered through celite
  3. concentrationthe filtrate concentrated
  4. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. extractionThe aqueous layer was extracted with further ethyl acetate
  6. washThe combined organic phases were washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-32bcf6637b00428bb7888de31e4d53f8
Source dataset
uspto-grants-2013_08
Patent number
US08501758B2

Reaction notes

Loading…