Ammonium Chloride → 1-{4-[(3-Amino-4,6-dimethyl-2-pyridinyl)amino]phenyl}-2-propanol

HRID 1454582

Reaction equation

HRID 1454582 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([OH:19])[CH3:18])=[CH:12][CH:11]=2)[C:3]=1[N+:20]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:20][C:3]1[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([OH:19])[CH3:18])=[CH:12][CH:11]=2)=[N:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 218757921-{4-[(4,6-Dimethyl-3-nitro-2-pyridinyl)amino]phenyl}-2-propanol

Product 1

HCID 218762711-{4-[(3-Amino-4,6-dimethyl-2-pyridinyl)amino]phenyl}-2-propanol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 1-{4-[(4,6-dimethyl-3-nitro-2-pyridinyl)amino]phenyl}-2-propanol (step 2, 500 mg, 1.66 mmol), iron powder (440 mg, 7.88 mmol), ammonium chloride (80 mg, 1.5 mmol) in ethanol/water (v/v, 31:8, 39 mL) was heated at reflux temperature for 2 h. The mixture was cooled and filtered through a pad of Celite. The filtrate was concentrated. The residue was diluted with dichloromethane (200 mL) and washed with water (2×100 mL). The organic layer was dried (MgSO4), and concentrated. Removal of solvent gave 450 mg (quant.) of the title compound as brown solids: TLC Rf0.10 (hexane/ethyl acetate=1:1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through a pad of Celite
  5. concentrationThe filtrate was concentrated
  6. additionThe residue was diluted with dichloromethane (200 mL)
  7. washwashed with water (2×100 mL)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. concentrationconcentrated
  10. customRemoval of solvent

Sources & evidence

ORD record
ord-3bd8d6e57c534c53ba9dfd302c6d256f
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Linked notes

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