Ammonium Chloride → 1,3-Benzenediamine, 2-methoxy-

HRID 131078

Reaction equation

HRID 131078 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[O:13][CH3:14])([O-])=O.[NH4+].[Cl-]>O.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 5977192,6-Dinitrophenyl methyl ether

Product 1

HCID 124029761,3-Benzenediamine, 2-methoxy-Yield 95%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

0.500 g (2.52 mmol) of compound 2,6-dinitroanisole was suspended in 40 mL of water together with 2.310 g (35.3 mmol) of Zn and 0.530 g (10.1 mmol) of NH4Cl. The solution was boiled for 2.5 h. After cooling to room temperature, the solution was extracted with ethyl acetate. The organic solution was dried with anhydrous Na2SO4 and distilled in vacuo to obtain 0.330 g (95%) of clean 2,6-diaminoanisole as a red oil. 1H NMR (CDCl3) δ 6.73 (t, J=7.9 Hz, 1H, Ar—H), 6.19 (d, J=7.9 Hz, 2H, Ar—H), 3.78 (s, 3H, O—CH3), 3.73 (br. s, 4H, Ar—NH2). 13C NMR (CDCl3) δ 140.3, 134.9, 125.2, 106.6, 58.6.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialThe organic solution was dried with anhydrous Na2SO4
  3. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-6f19936467724c4395edc034ea960fd7
Source dataset
uspto-grants-2008_06
Patent number
US07384789B2

Linked notes

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