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

HRID 987845Notes

Reaction equation

HRID 987845 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 1 N 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 1 N NaOH
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-370c5d1371864e4eba94863d0104b9a6
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

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