Ethanol → 4-Amino-3-methylbenzonitrile

HRID 1893537Notes

Reaction equation

HRID 1893537 reaction equation
C(O)C.O.[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[N+:14]([O-])=O)[C:9]#[N:10]>C(O)(=O)C>[NH2:14][C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[CH3:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 28014343-Methyl-4-nitrobenzonitrile

Product 1

HCID 70103164-Amino-3-methylbenzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

To an ethanol (500 ml)-water (60 ml)-acetic acid (30 ml) mixed solvent were added 3-methyl-4-nitrobenzonitrile (8.40 g, 51.8 mmol) and reduced iron (18 g, 322 mmol), and the mixture was stirred with heating at 85° C. for 3 hr. The reaction mixture was cooled, filtered through celite, and the solution was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate, washed with diluted aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (6.37 g, yield 93%) as a pale-yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionThe obtained residue was diluted with ethyl acetate
  5. washwashed with diluted aqueous sodium hydroxide solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93dc35b459eb46f190faf0021ac956fa
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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