Hydrochloric Acid → 4-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]-N-nitrosoaniline

HRID 1746098Notes

Reaction equation

HRID 1746098 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[N:15][CH:16]=2)=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+].[N:24]([O-])=[O:25].[Na+]>>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:24]=[O:25])=[CH:16][N:15]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 7784464-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]anilineHCID 23668193Sodium Nitrite

Product 1

HCID 31114194-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]-N-nitrosoanilineYield 85%

Conditions

Temperature
30 °C

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%.

Workup

  1. dissolutiondissolution
  2. temperaturecooled with ice-water bath to 0-5° C.
  3. additionAfter dropwise addition
  4. stirringstirred for 1 h
  5. filtrationsuction filtrated
  6. washwashed with water
  7. customto obtain light yellow solid powder
  8. customdried

Sources & evidence

ORD record
ord-6f5498567092485a99a73e7794c52fe0
Source dataset
uspto-grants-2015_10
Patent number
US09149467B2

Reaction notes

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