Sodium borohydride → N-(o-Chlorobenzyl)-2-methyl-3-chloroaniline

HRID 261823Notes

Reaction equation

HRID 261823 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH:4]=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH3:13].[BH4-].[Na+]>CO.O>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH3:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13017551N-(o-Chlorobenzylidene)-2-methyl-3-chloroaniline

Product 1

HCID 21321344N-(o-Chlorobenzyl)-2-methyl-3-chloroaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of N-(o-chlorobenzylidene)-2-methyl-3-chloroaniline (0.038 mole) is brought to reflux in 100 cc of absolute methanol. An equivalent of sodium borohydride (1.5 g.) is added in portions and refluxing is continued for 15 mins. The reaction mixture is cooled and diluted with an equal volume of cold water to precipitate a solid. This material is collected, washed with H2O and air dried. Recrystallization from ethanol gives N-(o-Chlorobenzyl)-2-methyl-3-chloroaniline. m.p. 63°-66° C.

Workup

  1. temperaturerefluxing
  2. temperatureThe reaction mixture is cooled
  3. customto precipitate a solid
  4. customThis material is collected
  5. washwashed with H2O and air
  6. customdried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7a8529161f27459898c0d6297c3f8657
Source dataset
uspto-grants-1979_05
Patent number
US04152452

Reaction notes

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