Dimethylformamide → 4-Amino-3-methyl-5-nitrobenzonitrile

HRID 470357Notes

Reaction equation

HRID 470357 reaction equation
Br[C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:4]([CH3:12])[CH:3]=1.[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:6][C:5]1[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]([C:13]#[N:14])=[CH:3][C:4]=1[CH3:12]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 5226794-Bromo-2-methyl-6-nitroaniline

Product 1

HCID 220210074-Amino-3-methyl-5-nitrobenzonitrileYield 73%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

A suspension of 4-bromo-2-methyl-6-nitroaniline (11.5 g, 50 mmol), Zn(CN)2 (770 mg, 150 mmol), and Pd(PPh3)4 (2.32 g, 2.0 mmol) in DMF (100 mL) was sealed and heated at 120° C. for 70 h. After cooled down to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography with CH2Cl2 to afford the title compound (6.4 g, 73%). ESI-MS m/z 178 (MH+).

Workup

  1. customwas sealed
  2. temperatureAfter cooled down to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by chromatography with CH2Cl2

Sources & evidence

ORD record
ord-6a57b9c642fc402d95f2c80ea64a5bff
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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