Reaction #1833280

Reaction equation

NaNO2

5-(2-p-methylphenylaminoethyl)-2-methylpyridine

HCl

NaHCO3

→

2-methyl-5-(N-nitroso-2-p-methylphenylaminoethyl)pyridine

Yield 85.0%

Conditions

Workup

1. 1
   workup.DISSOLUTIONdissolution
2. 2
   Temperaturecooled with ice-water bath to 0-5° C.
3. 3
   workup.ADDITIONAfter dropwise addition
4. 4
   workup.STIRRINGstirred for 1 h
5. 5
   Filtrationsuction filtrated
6. 6
   Washwashed with water
7. 7
   Otherto obtain light yellow solid powder
8. 8
   Otherdried

Procedure

To a three-necked bottle, 5-(2-p-methylphenylaminoethyl)-2-methylpyridine 4.5 g and 2N HCl 200 ml was added, heated to 30° C. and stirred to complete dissolution, then cooled with ice-water bath to 0-5° C., added dropwise with NaNO2 aqueous solution (13.8 g of NaNO2 dissolved in 50 ml of water). After dropwise addition, the temperature was elevated and the reaction was performed at room temperature for 1 h. To the reaction liquor, saturated NaHCO3 solution was slowly added dropwise until no gas generated. A great quantity of solid appeared, stirred for 1 h, suction filtrated, washed with water to obtain light yellow solid powder, dried and weighed to obtain 2-methyl-5-(N-nitroso-2-p-methylphenylaminoethyl)pyridine 4.3 g. Yield was about 85%.

Source