Water → HCID 22721178, compound

HRID 1582478Notes

Reaction equation

HRID 1582478 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][C:4]=1[O:10][CH2:11][CH3:12].O.[CH3:15][N:16](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([C:15]#[N:16])=[CH:5][C:4]=1[O:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 22721128HCID 22721128, compound

Product 1

HCID 22721178HCID 22721178, compoundYield 38%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

N,N-dimethyl-2-ethoxy-4-iodo-aniline (0.75 g, 2.58 mmol) was dissolved in DMF (4 mL). Zinc cyanide (0.18 g, 1.54 mmol) was added. Argon was passed through the mixture for 10 min. Tetrakis(triphenylphosphine)palladium (148 mg, 0.13 mmol) was added and the mixture was heated at 110° C. for 24 h. The reaction mixture was cooled and poured into water. The mixture was extracted with ethyl acetate, washed with brine and dried over magnesium sulfate. Evaporation of the solvents and chromatography of the residue over silica gel using 20% ethyl acetate in hexanes gave N,N-dimethyl-2-ethoxy-4-cyano-aniline (187 mg, 38%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvents and chromatography of the residue over silica gel using 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bca08c04225d4b099616b75a30762793
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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