4-(Methylamino)-3-nitrobenzonitrile → 3-Amino-4-(methylamino)benzonitrile

HRID 1241944Notes

Reaction equation

HRID 1241944 reaction equation
[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[N+:11]([O-])=O.[H][H]>CCOC(C)=O.[Pd]>[NH2:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[NH:2][CH3:1])[C:7]#[N:8]

Participants

5

Reactant 2

HCID 46007154-(Methylamino)-3-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 27797313-Amino-4-(methylamino)benzonitrileYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Methylamino-3-nitrobenzonitrile (0.18 g, 1.0 mmol) was dissolved in EtOAc (10 mL) and placed in a closed vessel. 10% Pd/C (50 mg, 5 mol %) was added and the mixture was hydrogenated via a hydrogen-filled balloon that was affixed to the vessel. After 2 h the mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield the title product (0.14 g, 93%) as an off-white solid, which was used without further purification. 1H-NMR (CDCl3): δ 7.19 (1H, dd), 6.92 (1H, d), 6.57 (1H, d), 4.04 (1H, br s), 3.30 (2H, br s), 2.91 (3H, br s); TLC (5:95 MeOH/DCM Rf 0.33).

Workup

  1. customplaced in a closed vessel
  2. additionfilled balloon that
  3. filtrationAfter 2 h the mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac2e0831d14d48288a2d555e2d60cde2
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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