5-Chloro-2-nitroanisole → Benzenamine, 4-chloro-2-methoxy-

HRID 1479128Notes

Reaction equation

HRID 1479128 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([O:8][CH3:9])[CH:7]=1.C([O-])=O.[NH4+]>[Pt].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 811105-Chloro-2-nitroanisoleHCID 2723923Ammonium formate

Product 1

HCID 7143Benzenamine, 4-chloro-2-methoxy-

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-chloro-2-nitroanisole (1.0 g, Sigma-Aldrich), ammonium formate (3.36 g, Alfa-Aesar) and 10% platinum on carbon (100 mg) in MeOH (10 mL) was heated to reflux for 45 minutes then cooled to room temperature and filtered through celite, washing with MeOH. The filtrates were concentrated and the residue was dissolved in EtOAc and water. The organics were dried (MgSO4) and concentrated to a brown oil. The material was absorbed onto silica and columned eluting ethyl acetate/heptane mixtures to give the product as a brown oil. Yield: 0.7 g. 1H NMR (400 MHz, CDCl3): δ 6.72-6.78 (2H, m, ArH), 6.58-6.62 (1H, m, ArH), 3.83 (3H, s, OMe).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 45 minutes
  3. filtrationfiltered through celite
  4. washwashing with MeOH
  5. concentrationThe filtrates were concentrated
  6. dissolutionthe residue was dissolved in EtOAc
  7. dry with materialThe organics were dried (MgSO4)
  8. concentrationconcentrated to a brown oil
  9. customThe material was absorbed onto silica
  10. washcolumned eluting ethyl acetate/heptane

Sources & evidence

ORD record
ord-e5cb25efd55a4cd8b694adafd8087e58
Source dataset
uspto-grants-2016_08
Patent number
US09406886B2

Reaction notes

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