Methanol → 4-(Aminomethyl)-2-chloro-6-methylaniline

HRID 2423340Notes

Reaction equation

HRID 2423340 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:11].CO>C1COCC1>[NH2:7][CH2:6][C:5]1[CH:8]=[C:9]([CH3:10])[C:2]([NH2:1])=[C:3]([Cl:11])[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 27353014-Amino-3-chloro-5-methylbenzonitrile

Product 1

HCID 552557664-(Aminomethyl)-2-chloro-6-methylanilineYield 3.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-3-chloro-5-methyl-benzonitrile (499.4 mg, 3.00 mmol) and Borane-THF complex (4 eq, 12.04 mmol, 12.04 ml) were added in THF. The reaction mixture was stirred for 3 hrs in reflux. After confirming the completion of the reaction, MeOH was added slowly added in the mixture. MeOH was removed in vacuo. The residue was extracted with ethyl acetate. A combined organic layer was washed with H2O and brine, dried with Na2SO4, concentrated in vacuo to yield 4-Aminomethyl-2-chloro-6-methyl-phenylamine (19.4 mg), as a yellow syrup.

Workup

  1. temperaturein reflux
  2. additionwas added slowly
  3. additionadded in the mixture
  4. customMeOH was removed in vacuo
  5. extractionThe residue was extracted with ethyl acetate
  6. washA combined organic layer was washed with H2O and brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1dd85a91453840d3ad98b87b9c11126c
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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