2-Amino-4-nitrobenzonitrile → HCID 68459146, compound

HRID 379533Notes

Reaction equation

HRID 379533 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5])#[N:2].[I-].C[N:15](C)N(C)C>CS(C)=O>[C:1]([C:3]1([NH2:15])[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:4]1[NH2:5])#[N:2]

Participants

4

Reactant 2

HCID 111478972-Amino-4-nitrobenzonitrileHCID 18366544HCID 18366544, compound

Product 1

HCID 68459146HCID 68459146, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-cyano-5-nitroaniline (435 mg, 2.67 mmol) in dimethylsulfoxide (25 ml) was added tetramethylhydrazine iodide(534 mg, 2.67 mmol) and sodium t-pentoxide (880 mg, 8.01 mmol). The mixture was stirred at room temperature for 12 hrs., the reaction was quenched with 10% HCl. Precipitated solids were filtered and the remaining solution was extracted with ethyl acetate, the solvent was evaporated and chromatography of the resulting solid on silica gel(25%EtOAc/Hexane) gave the desired product (254 mg, 53%). 1H NMR (CD3COCD3): δ7.49 (d, 1H), 7.03 (bs, 2H), 6.80 (d, 1H), 5.78(bs, 2H).

Workup

  1. custom, the reaction was quenched with 10% HCl
  2. customPrecipitated solids
  3. filtrationwere filtered
  4. extractionthe remaining solution was extracted with ethyl acetate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4238e1291662496daea5c27477ef1a8e
Source dataset
uspto-grants-2001_10
Patent number
US06300325B1

Reaction notes

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