Hydrochloric Acid → 4-Amino-2-methoxybenzonitrile

HRID 1173550

Reaction equation

HRID 1173550 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].Cl.C(=O)([O-])O.[Na+]>C(O)C.[Fe]>[NH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2918672-Methoxy-4-nitrobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 2327354-Amino-2-methoxybenzonitrileYield 73.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

2-Methoxy-4-nitrobenzonitrile (5.0 g) and iron powder (7.84 g) were suspended in ethanol (150 mL), and concentrated hydrochloric acid (35 mL) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 3 hr, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the obtained solid was washed with hexane to give the title compound as a red-brown solid (yield: 3.05 g, 73%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. washthe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-bb664db5d40d4656a5b892e7a08a54b1
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Linked notes

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