2,4-Dichloro-6-nitrophenol → 2-Amino-4,6-dichlorophenol

HRID 612687Notes

Reaction equation

HRID 612687 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:10][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[C:5]=1[OH:9]

Participants

5

Reactant 3

HCID 118712,4-Dichloro-6-nitrophenolHCID 14798Sodium HydroxideHCID 24479Stannous Chloride

Product 1

HCID 106992-Amino-4,6-dichlorophenolYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,6-dichloro-2-nitrophenol(1 g, 4.8 mmol) and tin (II) chloride (3.2 g, 14.4 mmol) in ethanol(50 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2Cl2) gave the desired product(685 mg, 80%). 1H NMR (CD3OD): δ 6.75 (s,1H), 6.61 (s, 1H).

Workup

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7636cdbfee224944902cdb85f44b6dec
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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