Water → 4-Amino-2,6-dichlorobenzonitrile

HRID 1486582Notes

Reaction equation

HRID 1486582 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([Cl:13])[C:3]=1[C:4]#[N:5].[Cl-].[NH4+].O>CO.[Fe]>[NH2:10][C:8]1[CH:7]=[C:6]([Cl:13])[C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 155276272,6-Dichloro-4-nitrobenzonitrile

Product 1

HCID 596359894-Amino-2,6-dichlorobenzonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A solution of 2,6-dichloro-4-nitrobenzonitrile (2.46 g, 11.3 mmol, Eq: 1.00), iron (3.17 g, 56.7 mmol, Eq: 5) and ammonium chloride (6.06 g, 113 mmol, Eq: 10) in methanol (30 mL)/water (10 mL) was heated at reflux o/n. TLC shows incomplete reaction. Continued heating at 100 deg for 6 hr, then 60 deg overnight. The reaction mixture was filtered over Celite. The filtrate was suspended in ethyl acetate to give insoluble solid. The slurry was concentrated to dryness, suspended in water, filtered, and rinsed with water. The solid was transferred to a round bottom flask, suspended in benzene, and concentrated. An additional portion of benzene was added and concentrated once more to give 1.37 g (65%) of desired product as a light brown solid.

Workup

  1. temperatureat reflux o/n
  2. customreaction
  3. temperatureContinued heating at 100 deg for 6 hr
  4. custom60 deg overnight
  5. filtrationThe reaction mixture was filtered over Celite
  6. customto give insoluble solid
  7. concentrationThe slurry was concentrated to dryness
  8. filtrationfiltered
  9. washrinsed with water
  10. customThe solid was transferred to a round bottom flask
  11. concentrationconcentrated
  12. additionAn additional portion of benzene was added
  13. concentrationconcentrated once more

Sources & evidence

ORD record
ord-fb095954dc934f73aa32e1837b0576c6
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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