Hydrochloric Acid → 4-Amino-3-chlorobenzonitrile

HRID 1607661Notes

Reaction equation

HRID 1607661 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:3]=1[NH:4]C(=O)C.Cl>C(O)C>[NH2:4][C:3]1[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2735721HCID 2735721, compound

Product 1

HCID 5198964-Amino-3-chlorobenzonitrileYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2'-chloro-4'-cyanoacetanilide (12.5 g) and concentrated hydrochloric acid (10 ml) in ethanol (50 ml) was refluxed for 30 minutes, and concentrated under reduced pressure. The residue was dissolved in water, adjusted to pH 9 with 4N-sodium hydroxide aqueous solution, and extracted with chloroform. The extract was concentrated and the residue was subjected to column chromatography on silica gel (150 g) eluting with chloroform. The fractions containing the desired compound were combined and concentrated to give a powder of 4-amino-3-chlorobenzonitrile (5.7 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with chloroform
  5. concentrationThe extract was concentrated
  6. washeluting with chloroform
  7. additionThe fractions containing the desired compound
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4940746322634067b76388d03ffb1fde
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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