Ammonium Chloride → 3-Cyanomethyl-2,4,6-trimethylaniline

HRID 2229913Notes

Reaction equation

HRID 2229913 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([CH3:15])=[C:6]([N+:12]([O-])=O)[C:7]([CH3:11])=[CH:8][C:9]=1[CH3:10])#[N:2].[Cl-].[NH4+]>CO.[Zn]>[C:1]([CH2:3][C:4]1[C:5]([CH3:15])=[C:6]([C:7]([CH3:11])=[CH:8][C:9]=1[CH3:10])[NH2:12])#[N:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 106796973-Cyanomethyl-1-nitro-2,4,6-trimethylbenzene

Product 1

HCID 108449753-Cyanomethyl-2,4,6-trimethylanilineYield 69%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-cyanomethyl-1-nitro-2,4,6-trimethylbenzene (5.8 g in methanol (150 mL) were sequentially added ammonium chloride (6 g in 50 mL of water), zinc powder (6 g). The exothermic reaction was vigorously stirred until it was back to RT (2 h). To work up the crude mixture was filtered off and the cake was washed with methanol. The methanolic solutions were concentrated and the residue partitioned between ethyl acetate and 1N NaOH. The organic layer was dried over MgSO4 and concentrated to give 3-cyanomethyl-2,4,6-trimethylaniline as a light brown solid (3.4 g, 69%).

Workup

  1. customThe exothermic reaction
  2. customwas back to RT
  3. custom(2 h)
  4. filtrationwas filtered off
  5. washthe cake was washed with methanol
  6. concentrationThe methanolic solutions were concentrated
  7. customthe residue partitioned between ethyl acetate and 1N NaOH
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-370b37cd68d548e287ad552ad863560f
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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