Ethyl Acetate → 6-Amino-2,3-dichlorophenol

HRID 612689Notes

Reaction equation

HRID 612689 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([OH:9])[C:7]=1[Cl:8].[Sn](Cl)Cl.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[NH2:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:7]([Cl:8])[C:6]=1[OH:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 105602752,3-Dichloro-6-nitrophenol

Product 1

HCID 122132156-Amino-2,3-dichlorophenolYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5,6-dichloro-2-nitrophenol(1.8 g, 8.7 mmol) and tin (II) chloride (5.8 g, 26.1 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 extrated 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(1.4 mg, 90%). 1H NMR (CD3OD): δ 6.71 (d, 1H), 6.45 (d, 1H).

Workup

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

Sources & evidence

ORD record
ord-23b874d0f4a54d788098c8af04c91db2
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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