Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate → Methyl 3,5-diamino-4-(4-methoxyphenoxy)benzoate

HRID 564839

Reaction equation

HRID 564839 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:23]([O-])=O)[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O.[H][H]>C(O)(=O)C.[Pd]>[NH2:23][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([NH2:1])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 9819693Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 9947870Methyl 3,5-diamino-4-(4-methoxyphenoxy)benzoateYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a Parr shaker bottle containing a suspension of methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate (20.2 g; 77.5 mmol) in glacial acetic acid (80 ml) was added 10% palladium on charcoal (0.7 g). The bottle was shaken under an atmosphere of hydrogen (3 atm) until no more hydrogen was consumed. The catalyst was filtered off and the resulting solution concentrated to approximately 10 ml. The residue was dissolved in acetone (50 ml) and heated on a steam bath while water (100 ml) was added in portions. Upon cooling, medium brown needles formed which were collected by suction filtration and dried to give 7.1 g (86%) of methyl 3,5-diamino-4-(4-methoxyphenoxy)benzoate. 300 MHz 1H NMR (CDCl3) d 3.73 (s, 3H, OCH3), 3.80 (bs, 4H, ArNH2) 3.86 (s, 3H, OCH3), 6.84 (m, 4H, ArH), 6.91 (s, 2H, ArH).

Workup

  1. additionTo a Parr shaker bottle containing
  2. customwas consumed
  3. filtrationThe catalyst was filtered off
  4. concentrationthe resulting solution concentrated to approximately 10 ml
  5. dissolutionThe residue was dissolved in acetone (50 ml)
  6. temperatureheated on a steam bath while water (100 ml)
  7. additionwas added in portions
  8. temperatureUpon cooling
  9. custommedium brown needles formed which
  10. filtrationwere collected by suction filtration
  11. customdried

Sources & evidence

ORD record
ord-de484765b90a4e72846db3c105cf1216
Source dataset
uspto-grants-2001_01
Patent number
US06169104A

Linked notes

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