Ammonium Chloride → (4-Benzyloxy-phenyl)-methyl-(4-methyl-2-amino-phenyl)-amine

HRID 607245Notes

Reaction equation

HRID 607245 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH3:26])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[N+:23]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>O.C(O)C.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH3:26])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[NH2:23])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 66808474(4-Benzyloxy-phenyl)-methyl-(4-methyl-2-nitro-phenyl)-amine

Product 1

HCID 66808542(4-Benzyloxy-phenyl)-methyl-(4-methyl-2-amino-phenyl)-amine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of the product from Example 133B (129.4 mg, 0.3714 mmol), iron powder (128 mg, 2.284 mmol), ammonium chloride (130 mg, 2.433 mmol) in water (1 mL) and ethanol (2 mL) was heated at 70° under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature and vacuum filtered, washing the residue with methanol. The filtrate was concentrated under vacuum and azeotroped with toluene (50 mL). The residue was purified by silica gel flash chromatography using methylene chloride as eluent to provide the title compound as a waxy solid (85 mg, 72%).

Workup

  1. temperaturewas heated at 70° under a nitrogen atmosphere for 1 hour
  2. filtrationvacuum filtered
  3. washwashing the residue with methanol
  4. concentrationThe filtrate was concentrated under vacuum
  5. customazeotroped with toluene (50 mL)
  6. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3f2b1f8af1b746c882a35ca304cf6934
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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