Methanol → HCID 596025, compound

HRID 601693Notes

Reaction equation

HRID 601693 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[C:8]([CH3:11])[C:7]([CH3:12])=[C:6]([CH3:13])[C:5]=1[CH3:14])([O-])=O.CO.[Cl-].[NH4+]>[Zn].O>[CH3:10][C:9]1[C:4]([NH2:1])=[C:5]([CH3:14])[C:6]([CH3:13])=[C:7]([CH3:12])[C:8]=1[CH3:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 518726Pentamethylnitrobenzene

Product 1

HCID 596025HCID 596025, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A one neck 2000 ml round bottom flask was charged with 50 grams of 1-nitro-2,3,4,5,6-pentamethylbenzene and 1000 ml methanol. A solution of 50 g of ammonium chloride and 200 ml of water was then added. Zinc dust (50 g) was then added in portions. The mixture was allowed to stir for 20 hours. The solids were filtered and the solvent was removed from the mother liquor. The product was purified by silica gel column with dichlormethane as the eluent. The good fractions are combined to yield pentamethylaniline as a white solid.

Workup

  1. filtrationThe solids were filtered
  2. customthe solvent was removed from the mother liquor
  3. customThe product was purified by silica gel column with dichlormethane as the eluent

Sources & evidence

ORD record
ord-10d1d27a7d9543ba9395582f621fe4d0
Source dataset
uspto-grants-2011_03
Patent number
US07902374B2

Reaction notes

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