2-Aminobenzonitrile → HCID 21822800, compound

HRID 1350493Notes

Reaction equation

HRID 1350493 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15].O.[OH-].[Li+]>CS(C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 729132-AminobenzonitrileHCID 738951-Fluoro-2-nitrobenzeneHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 21822800HCID 21822800, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

Combine 1-fluoro-2-nitro-benzene (5.00 g, 35.44 mmol), 2-amino-benzonitrile (4.19 g, 35.44 mmol), lithium hydroxide monohydrate (2.97 g, 70.87 mmol) and DMSO (50.0 ml). Stir the mixture at 55 ° C. for 19 hours then cool to ambient temperature. Pour the mixture onto ice chips and stir for 1 hour. Remove the resulting precipitate by vacuum filtration. Dry the precipitate under vacuum to give 6.14 g (72%) of an orange solid: mp 134–138°.

Workup

  1. temperaturethen cool to ambient temperature
  2. additionPour the mixture onto ice chips
  3. stirringstir for 1 hour
  4. customRemove the resulting precipitate
  5. filtrationby vacuum filtration
  6. customDry the precipitate under vacuum

Sources & evidence

ORD record
ord-3b7ca6f4df3e4db8a27f4014a4c6a298
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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