N-Methylaniline → Propanenitrile, 3-(methylphenylamino)-

HRID 275088Notes

Reaction equation

HRID 275088 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9](#[N:12])[CH:10]=[CH2:11]>>[C:9]([CH2:10][CH2:11][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[N:12]

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 7855Acrylonitrile

Product 1

HCID 66748Propanenitrile, 3-(methylphenylamino)-

Conditions

Temperature
120 °C

Procedure

1071.5 Parts by weight (10 mol) of N-methylaniline and 15.0 parts by weight of Tonsil® K 10 are placed in a 3-neck stirred flask fitted with a reflux condenser and inlet tube. The mixture is heated to 120° C. and 265.3 parts by weight (5 mol) of acrylonitrile are added at this temperature via the inlet tube. The reaction mixture is subsequently stirred for 18 hours at from 120° to 130° C. and then cooled to 60° C. The catalyst is filtered off and the liquid phase is subjected to fractional distillation. 47.7 parts by weight of acrylonitrile and 620.9 parts by weight of N-methylaniline are recovered and can be used again as starting material. The yield of N-β-cyanoethyl-N-methylaniline is 605.0 parts by weight ~75.5% conversion. The purity is 99.5% N-β-cyanoethyl-N-methylaniline.

Workup

  1. customfitted with a reflux condenser and inlet tube
  2. stirringThe reaction mixture is subsequently stirred for 18 hours at from 120° to 130° C.
  3. temperaturecooled to 60° C
  4. filtrationThe catalyst is filtered off
  5. distillationthe liquid phase is subjected to fractional distillation
  6. custom47.7 parts by weight of acrylonitrile and 620.9 parts by weight of N-methylaniline are recovered

Sources & evidence

ORD record
ord-cdb1d161d3f0402f9aee568218790e9a
Source dataset
uspto-grants-1995_02
Patent number
US05391804

Reaction notes

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