Ammonia → HCID 68557310, compound

HRID 1967582Notes

Reaction equation

HRID 1967582 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:18]([O-])=O)[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.N>Cl.CCO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 99729021,3-Dichloro-2-(4-methoxyphenoxy)-5-nitrobenzene

Product 1

HCID 68557310HCID 68557310, compoundYield 119.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of stannous chloride dihydrate (32.38 g, 0.14 mol) in concentrated HCl (11 mL) was added 3,5-dichloro-4-(4-methoxy-phenoxy)nitrobenzene (11.3 g, 0.03 mol) in EtOH (56.5 mL). The reaction mixture was refluxed for about 2 h. The resulting mixture was brought at 20-30° C. and diluted with ethyl acetate. The mixture was made alkaline with ammonia solution. Resulting solid was filtered through cellite. The organic phase was washed with water, brine, dried over sodium sulphate, filtered and concentrated to give 3,5-Dichloro-4-(4-methoxy-phenoxy)-phenylamine (10.2 g; % Yield: 99%).

Workup

  1. temperatureThe reaction mixture was refluxed for about 2 h
  2. customwas brought at 20-30° C.
  3. customResulting solid
  4. filtrationwas filtered through cellite
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5a340bffbfb94fc68fb96a5000cf20d0
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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