Hydrochloric Acid → 2,3-Dimethyl-6-nitrobenzylamine

HRID 979524Notes

Reaction equation

HRID 979524 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]#[N:5].Cl>O1CCCC1>[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135090072,3-Dimethyl-6-nitrobenzonitrile

Product 1

HCID 150650752,3-Dimethyl-6-nitrobenzylamineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane-tetrahydrofuran complex (94.6 g, 1.1 mole) in tetrahydrofuran (1100 mL) was added dropwise to a stirred solution of 2,3-dimethyl-6-nitrobenzonitrile (96 g, 0.55 mole) in dry tetrahydrofuran (650 mL) maintained under an atmosphere of argon. After stirring overnight, 10% hydrochloric acid solution (1300 mL) was added dropwise and the mixture heated to reflux. After 30 minutes, the tetrahydrofuran was distilled off, the residue filtered to remove insoluble material and the filtrate made basic with concentrated ammonium hydroxide solution (350 mL). The mixture was extracted with diethyl ether (2×500 mL), the combined extracts washed with water (2×400 mL), dried over potassium carbonate and concentrated to afford 2,3-dimethyl-6-nitrobenzyl amine (93.85 g, 95%) as an oil used without further purification as follows.

Workup

  1. temperaturemaintained under an atmosphere of argon
  2. temperaturethe mixture heated to reflux
  3. waitAfter 30 minutes
  4. distillationthe tetrahydrofuran was distilled off
  5. filtrationthe residue filtered
  6. customto remove insoluble material
  7. extractionThe mixture was extracted with diethyl ether (2×500 mL)
  8. washthe combined extracts washed with water (2×400 mL)
  9. dry with materialdried over potassium carbonate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f71e9624de2c48b39ff2d559f0bd44ea
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

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