Sodium Hydroxide → 2-Amino-3-chlorophenol

HRID 612684Notes

Reaction equation

HRID 612684 reaction equation
[Cl:1][C:2]1[C:3]([N+:9]([O-])=O)=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 136221703-Chloro-2-nitrophenol

Product 1

HCID 198289622-Amino-3-chlorophenolYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-chloro-2-nitrophenol(250 mg, 1.4 mmol) and tin (II) chloride (1.2 g, 5.3 mmol) in ethanol(50 mL) was heated at 80° C. under argon. After 2 hours, the starting material has 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(143 mg, 69%). 1H NMR (CD3OD): δ 6.75 (t, 1H), 6.70 (d, 1H), 6.65 (d, 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-5f926ab66b5b4e599c36d211653a2c2c
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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