Stannous Chloride → 4-(Benzyloxy)-3,5-dichloroaniline

HRID 883817

Reaction equation

HRID 883817 reaction equation
[Sn](Cl)Cl.[CH2:4]([O:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([N+:19]([O-])=O)=[CH:14][C:13]=1[Cl:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(O)C.C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:4]([O:11][C:12]1[C:13]([Cl:22])=[CH:14][C:15]([NH2:19])=[CH:16][C:17]=1[Cl:18])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 24479Stannous ChlorideHCID 9855836Potassium sodium tartarateHCID 595097642-(Benzyloxy)-1,3-dichloro-5-nitrobenzene

Product 1

HCID 185431714-(Benzyloxy)-3,5-dichloroaniline

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

Tin(II) chloride (22 g, 98 mmol) was added to a stirring solution of 2-(benzyloxy)-1,3-dichloro-5-nitrobenzene (5.8 g, 19 mmol) in ethanol (80 mL), and the resulting suspension was heated to 70° C. After 1 h the mixture was cooled to room temperature and diluted with ethyl acetate (200 mL). The mixture was poured into brine (100 mL) and the resulting emulsion stirred with sodium potassium tartrate solution (200 mL). The mixture was extracted with ethyl acetate and the combined organic layers dried (MgSO4), filtered and concentrated in vacuo to afford 4-(benzyloxy)-3,5-dichloroaniline that was used directly in the next step without purification.

Workup

  1. temperatureAfter 1 h the mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe combined organic layers dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3cc40db0e4aa49bfb82c4e603f980a5f
Source dataset
uspto-grants-2012_08
Patent number
US08236984B2

Linked notes

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