Sodium Hydroxide → 2-Hydroxy-3-cyano-4-chloroaniline

HRID 650108Notes

Reaction equation

HRID 650108 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([C:11]#[N:12])[C:5]=1[OH:13])([O-])=O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([C:11]#[N:12])[C:5]=1[OH:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 217143992-Nitro-5-chloro-6-cyanophenol

Product 1

HCID 217144052-Hydroxy-3-cyano-4-chloroanilineYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-nitro-5-chloro-6-cyanophenol (750 mg, 3.78 mmol) and tin (II) chloride (2.6 g, 11.4 mmol) in ethanol(50ml) is heated at 80° C. under argon. After 2 hours, the starting material has disappeared and the solution is allowed to cool down and then poured into ice. The pH is 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(410 mg, 65%). 1H NMR (CD30D): δ8 6.89 (d, 1H), 6.88 (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-fa21cba43fb14add884028d463a67b32
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

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