Dimethyl Sulfide → (2-Methyl-4-nitrophenyl)methanamine

HRID 1428759Notes

Reaction equation

HRID 1428759 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].S(C)C>O1CCCC1>[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 43463672-Methyl-4-nitrobenzonitrile

Product 1

HCID 20285976(2-Methyl-4-nitrophenyl)methanamineYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-methyl-4-nitrobenzonitrile (407 mg, 2.510 mmol) in tetrahydrofuran was added 2M BH3.SMe2 in tetrahydrofuran (2.1 mL). The reaction mixture was stirred for 15 h at 70° C. The mixture was cooled to room temperature, then quenched by water. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give (2-methyl-4-nitrophenyl)methanamine (178 mg, 43%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched by water
  3. dissolutionThe mixture dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate removed in vacuo
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-6a39619e66bc49328662e870e489b077
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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