2-Amino-4-methylbenzonitrile → N-(2-cyano-5-methyl-phenyl)-2-methoxy-6-methyl-benzamide
Reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][O:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:14]=1[C:15](Cl)=[O:16]>N1C=CC=CC=1>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:2]=1[NH:1][C:15](=[O:16])[C:14]1[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:13]=1[O:12][CH3:11])#[N:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Amino-4-methyl-benzonitrile (15.4 g, 0.117 mol) was dissolved in 100 mL pyridine and cooled to 0° C. To this mixture was added dropwise 2-methoxy-6-methylbenzoyl chloride (24 g, 0.13 mol, 1.1 equiv). During the addition the temperature did not exceed 2° C. The reaction was stirred at room temperature for 48 hours. The mixture was poured into 400 mL ice water, and the precipitate was collected by filtration and washed with water. The crude product was dissolved in 600 mL CH2Cl2, and the solution was washed twice with 500 mL of a 1 N HCl solution and once with 400 mL of a saturated aq. NaCl solution. The CH2Cl2 layer was dried over Na2SO4, filtered, and concentrated to dryness to yield 25.44 g (0.09 mol, 77.6%) of N-(2-cyano-5-methyl-phenyl)-2-methoxy-6-methyl-benzamide.
Workup
- additionDuring the addition the temperature
- customdid not exceed 2° C
- filtrationthe precipitate was collected by filtration
- washwashed with water
- dissolutionThe crude product was dissolved in 600 mL CH2Cl2
- washthe solution was washed twice with 500 mL of a 1 N HCl solution and once with 400 mL of a saturated aq. NaCl solution
- dry with materialThe CH2Cl2 layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-5b589645bf58414ea8e2958e0cb47cb0
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283354B2
Reaction notes
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