Sodium Hydroxide → 5-Amino-2-chlorobenzonitrile

HRID 1591845Notes

Reaction equation

HRID 1591845 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5].[OH-].[Na+]>C(O)(C)C.Cl>[NH2:10][C:7]1[CH:8]=[CH:9][C:2]([Cl:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 109972345-Amino-2-chlorobenzonitrileYield 96%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 2-chloro-5-nitrobenzonitrile (10 g, 54.8 mmol) and stannous chloride dihydrate (56 g, 248.6 mmol) in isopropyl alcohol (125 mL) and concentrated hydrochloric acid solution (62.5 mL) was heated to reflux for 1 hour. The mixture was then cooled and neutralized with sodium hydroxide solution (2N). The aqueous layer was extracted with methylene chloride. The combined organic layers were dried over magnesium sulfate and concentrated to afford the title compound (8 g, 96%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was then cooled
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-85be48bb748a4ceea92ac3619c3976ad
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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