Ammonium Chloride → 2-Methyl-4-(2-pyrimidinylmethoxy)aniline

HRID 402692Notes

Reaction equation

HRID 402692 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)[O:5][CH2:6][C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[N:8]=[CH:9][CH:10]=[CH:11][N:12]=2)[CH:13]=[CH:14][C:15]=1[NH2:16]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 867083912-[(3-Methyl-4-nitrophenoxy)methyl]pyrimidine

Product 1

HCID 626995032-Methyl-4-(2-pyrimidinylmethoxy)anilineYield 99.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-[(3-methyl-4-nitrophenoxy)methyl]pyrimidine (0.18 g, 0.7 mmol) in ethanol (4.0 mL) and water (1.0 mL), iron (0.40 g, 7.2 mmol) and ammonium chloride (0.020 g, 0.37 mmol) were added. The mixture was refluxed for 1.5 h. Cooled to ambient temperature, the reaction mixture was filtered over Celite to remove unneeded materials and the filtrate was concentrated to afford 2-methyl-4-(2-pyrimidinylmethoxy)aniline (0.15 g, crude material) as solid.

Workup

  1. temperatureThe mixture was refluxed for 1.5 h
  2. filtrationthe reaction mixture was filtered over Celite
  3. customto remove unneeded materials
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-40efd4005d31432296f872f2bb583007
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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