Hydrochloric Acid → 5-Dimethylamino-2-nitrobenzylamine

HRID 64863Notes

Reaction equation

HRID 64863 reaction equation
FC(F)(F)C(O)=O.[BH4-].[Na+].[CH3:10][N:11]([CH3:23])[C:12]1[CH:13]=[CH:14][C:15]([N+:20]([O-:22])=[O:21])=[C:16]([CH:19]=1)[C:17]#[N:18].Cl>O1CCCC1>[CH3:10][N:11]([CH3:23])[C:12]1[CH:13]=[CH:14][C:15]([N+:20]([O-:22])=[O:21])=[C:16]([CH:19]=1)[CH2:17][NH2:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 202358405-(Dimethylamino)-2-nitrobenzonitrile

Product 1

HCID 202358395-Dimethylamino-2-nitrobenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution consisting of 120 ml of trifluoroacetic acid and 200 ml of tetrahydrofuran was added to a solution of 60 g of sodium borohydride in 300 ml of tetrahydrofuran under ice-cooling to a temperature of 15° C. or less. 63.4 of 5-dimethylamino-2-nitrobenzonitrile was added to the mixture, followed by stirring. After cooling the heat generated, the stirring was continued at room temperature overnight. 650 ml of a 10% aqueous solution of hydrochloric acid was then added thereto, followed by heat-refluxing for 1.5 hours. The tetrahydrofuran was removed by distillation under reduced pressure. The aqueous layer was washed with benzene, rendered alkaline with a sodium hydroxide aqueous solution, and extracted with chloroform. The extract was washed with water, dried and distilled off to remove the chloroform. The residue was purified by silica gel chromatography to obtain 33.4 g of 5-dimethylamino-2-nitrobenzylamine (melting point: 97°-98° C.).

Workup

  1. temperaturecooling to a temperature of 15° C. or less
  2. temperatureAfter cooling the heat
  3. temperatureby heat-refluxing for 1.5 hours
  4. customThe tetrahydrofuran was removed by distillation under reduced pressure
  5. washThe aqueous layer was washed with benzene
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. distillationdistilled off
  10. customto remove the chloroform
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-37edea4d20d6431ba47637f5b7c59747
Source dataset
uspto-grants-1986_09
Patent number
US04610987

Reaction notes

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