Hydrochloric Acid → 2-Amino-5-(4-chlorophenoxy)benzonitrile

HRID 363794

Reaction equation

HRID 363794 reaction equation
Cl.O.[N+:3]([C:6]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][C:7]=1[C:8]#[N:9])([O-])=O>C(O)C.[Fe]>[NH2:3][C:6]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 218248742-Nitro-5-(4-chlorophenoxy)benzonitrile

Product 1

HCID 218248512-Amino-5-(4-chlorophenoxy)benzonitrileYield 9.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.0 grams (0.035 mole) of iron powder, 1.0 mL of concentrated hydrochloric acid, 4.0 mL of water, in 30 mL of ethanol was stirred, and 2.5 grams (0.009 mole) of 2-nitro-5-(4-chlorophenoxy)benzonitrile was added slowly. Upon completion of addition, the reacton mixture was warmed to reflux where it stirred for about seven hours. After this time, the reaction mixture was allowed to cool to ambient temperature where it stirred for about 18 hours. The reaction mixture was then warmed and filtered through a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel, using 1:1 petroleum ether/methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.2 gram of 2-amino-5-(4-chlorophenoxy)benzonitrile, mp 116°-118° C. The NMR spectrum was consistent with the proposed structure. The reaction was repeated.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reacton mixture was warmed
  3. temperatureto reflux where it
  4. stirringstirred for about 18 hours
  5. temperatureThe reaction mixture was then warmed
  6. filtrationfiltered through a pad of diatomaceous earth
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. customThe residue was purified with column chromatography on silica gel
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd445489039b4aa1acc57c0da85a244e
Source dataset
uspto-grants-1999_02
Patent number
US05874579

Linked notes

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