3-Methyl-2-nitroanisole → 2-Methoxy-6-methylaniline

HRID 1389506

Reaction equation

HRID 1389506 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH3:12])([O-])=O>C(O)(=O)C.[Fe]>[CH3:12][O:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:4]=1[NH2:1]

Participants

4

Reactant 1

HCID 792913-Methyl-2-nitroanisole

Product 1

HCID 4592492-Methoxy-6-methylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Solid 2-nitro-3-methylanisole (20 g) is added portion to a hot (40°-60° C.) suspension of iron (30 g) in 20% acetic acid (400 ml). The mixture is heated on a steam bath for 40 min, filtered still hot and neutralized (after cooling) with 50% aqueous sodium hydroxide. The mixture is steam distilled (2 liters of water collected). The distillate is extracted with diethyl ether and the etheral solution is dried and evaporated to give an oily residue of 2-methoxy-6-methylbenzenamine: nmr (CDCl3) δ2.15 (s, 3H), 3.7 (s, 2H), 3.8 (s, 3H) and 6.7 (m, 3H).

Workup

  1. temperatureThe mixture is heated on a steam bath for 40 min
  2. filtrationfiltered still hot
  3. temperatureneutralized (after cooling) with 50% aqueous sodium hydroxide
  4. distillationdistilled
  5. custom(2 liters of water collected)
  6. extractionThe distillate is extracted with diethyl ether
  7. customthe etheral solution is dried
  8. customevaporated

Sources & evidence

ORD record
ord-d7378ab606ba4a589d1d7b2258d3be89
Source dataset
uspto-grants-1981_01
Patent number
US04244966

Linked notes

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