Sodium Hydroxide → 3-Amino-2,6-dichlorobenzonitrile

HRID 1508175Notes

Reaction equation

HRID 1508175 reaction equation
[Cl:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([Cl:13])[C:3]=1[C:4]#[N:5].[OH-].[Na+]>CN(C=O)C.O>[NH2:10][C:9]1[C:2]([Cl:1])=[C:3]([C:6]([Cl:13])=[CH:7][CH:8]=1)[C:4]#[N:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 44619322,6-Dichloro-3-nitrobenzonitrile

Product 1

HCID 154052993-Amino-2,6-dichlorobenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,6-dichloro-3-nitrobenzonitrile (1.38 mmol) and SnCl2 dihydrate (4.15 mmol) in 3 mL DMF was heated to 100° C. for 10 min under microwave conditions. The reaction mixture was diluted with water, basified with 1M NaOH solution to pH 11-12 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give the desired product as brown solid;

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a29fc1e4fa0244e293713bd7c3224fb4
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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