Potassium Iodide → HCID 66932383, compound

HRID 245095Notes

Reaction equation

HRID 245095 reaction equation
Br[C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[C-]#N.[Na+].[I-].[K+].[CH3:17][NH:18]CCNC>C1(C)C=CC=CC=1.[Cu]I.C(OCC)(=O)C.O>[NH2:6][C:5]1[C:7]([CH3:9])=[CH:8][C:2]([C:17]#[N:18])=[CH:3][C:4]=1[CH2:10][CH3:11]

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 9607614-Bromo-2-ethyl-6-methylaniline

Product 1

HCID 66932383HCID 66932383, compoundYield 99.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
118 °C

Procedure

A double-jacketed 4 L-flask is charged with 4-bromo-2-ethyl-6-methyl-aniline (324 g, 1.51 mol), sodium cyanide (100.3 g, 1.97 mol), potassium iodide (50.2 g, 0.302 mol) and copper(I)iodide (28.7 g, 0.151 mol). The flask is evacuated three times and refilled with nitrogen. A solution of N,N′-dimethylethylenediamine (191.5 mL, 1.51 mol) in toluene (750 mL) is added. The mixture is heated to 118° C. and stirred at this temperature for 21 h. The mixture is cooled to 93° C. and water (1250 mL) is added to obtain a solution. Ethyl acetate (1250 mL) is added at 22-45° C. and the layers are separated. The org. phase is washed with 10% aq. citric acid (2×500 mL) and water (500 mL). The separated org. phase is evaporated to dryness to afford 4-amino-3-ethyl-5-methyl-benzonitrile (240 g) as a metallic black solid; 1H NMR (CDCl3): δ1.29 (t, J=7.5 Hz, 3H), 2.19 (s, 3H), 2.52 (q, J=7.3 Hz, 2H), 4.10 (s br, 1H), 7.25 (s, 2H).

Workup

  1. customThe flask is evacuated three times
  2. additionrefilled with nitrogen
  3. temperatureThe mixture is cooled to 93° C.
  4. customto obtain a solution
  5. customthe layers are separated
  6. washphase is washed with 10% aq. citric acid (2×500 mL) and water (500 mL)
  7. customphase is evaporated to dryness

Sources & evidence

ORD record
ord-213d794eee5140a8807511225439abea
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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