1-Methylnaphthalene → 2-Amino-5-cyano-N,3-dimethylbenzamide

HRID 888251Notes

Reaction equation

HRID 888251 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9](Br)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].CC1C2C(=CC=CC=2)C=CC=1.[C-:25]#[N:26].[Na+]>CN(C)C1C=CN=CC=1.[Cu]I.O>[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([C:25]#[N:26])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

7

Reactant 3

HCID 70021-MethylnaphthaleneHCID 8929Sodium CyanideHCID 442275752-amino-5-bromo-N,3-dimethylbenzamide

Product 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

A 100-mL, three-necked flask equipped with a mechanical stirrer, thermometer and condenser was charged with 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (5.0 g, 0.020 mol, 99.1% purity) and 1-methylnaphthalene (20 g) while maintaining a flow of nitrogen through a gas inlet line connected to the condenser. The reaction mixture was stirred at room temperature, and powdered sodium cyanide (powdered just prior to use) (1.25 g, 0.024 mol, assuming 95% purity), copper(I) iodide (0.57 g, 0.0030 mol) and 4-(dimethylamino)pyridine (2.10 g, 0.017 mol) were added. The mixture was heated at 160 to 165° C. for 4.25 h and then allowed to cool to 25° C. Water (20 mL) was added dropwise to the reaction mixture over 5 minutes while stirring. After stirring for an additional 30 minutes, the reaction mixture was filtered, and the solid collected was washed with water (3×10 mL) and xylenes (10 mL), and then dried to a constant weight in a vacuum-oven at 50° C. to give the title compound as a light brown solid (3.9 g).

Workup

  1. customA 100-mL, three-necked flask equipped with a mechanical stirrer
  2. temperaturewhile maintaining a flow of nitrogen through a gas inlet line
  3. temperatureThe mixture was heated at 160 to 165° C. for 4.25 h
  4. temperatureto cool to 25° C
  5. stirringwhile stirring
  6. stirringAfter stirring for an additional 30 minutes
  7. filtrationthe reaction mixture was filtered
  8. customthe solid collected
  9. washwas washed with water (3×10 mL) and xylenes (10 mL)
  10. customdried to a constant weight in a vacuum-oven at 50° C.

Sources & evidence

ORD record
ord-812ba1dd127a4bbca14c717f9941bcc1
Source dataset
uspto-grants-2012_08
Patent number
US08247570B2

Reaction notes

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