Sodium Hydroxide → 3-(2-Methoxyethoxy)benzene-1,2-diamine

HRID 18542

Reaction equation

HRID 18542 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:7]=1[NH2:15].[OH-].[Na+]>C(OCC)(=O)C.C(O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[C:7]=1[NH2:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 593496042-(2-Methoxyethoxy)-6-nitroaniline

Product 1

HCID 684142223-(2-Methoxyethoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1 g 2-(2-Methoxy-ethoxy)-6-nitro-phenylamine in 10 mL ethyl acetate and 3 mL ethanol, 4.4 g SnCl2 dihydrate were added and the reaction mixture was heated to reflux for 6 h. Then, after cooling 50 mL 2 M NaOH were added and the inorganic precipitate was filtered and washed extensivley with ethyl acetate. The filtrate was extracted with exthyl acetate (3×100 ml), the combined organic layers were dried over MgSO4, and the solvents were removed under reduced pressure. The remaining product was pure enough for the next reaction step.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. additionwere added
  4. filtrationthe inorganic precipitate was filtered
  5. washwashed extensivley with ethyl acetate
  6. extractionThe filtrate was extracted with exthyl acetate (3×100 ml)
  7. dry with materialthe combined organic layers were dried over MgSO4
  8. customthe solvents were removed under reduced pressure
  9. customThe remaining product was pure enough for the next reaction step

Sources & evidence

ORD record
ord-7ca436af06dc497f9fc83b82dd2f06b1
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

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