Ammonia → 3-(4-Amino-3,5-dimethylphenyl)-2-propenenitrile

HRID 1847135Notes

Reaction equation

HRID 1847135 reaction equation
FC(F)(F)C(O)=O.[CH3:8][CH:9]1[CH:22]=[C:21]([CH:23]=[CH:24][C:25]#[N:26])[CH:20]=[C:19]([CH3:27])[C:10]1(C(O)=O)CNC1C=CC=CC=1.[NH3:31]>O>[CH3:8][C:9]1[CH:22]=[C:21]([CH:23]=[CH:24][C:25]#[N:26])[CH:20]=[C:19]([CH3:27])[C:10]=1[NH2:31]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 131732434HCID 131732434, compound

Product 1

HCID 573502333-(4-Amino-3,5-dimethylphenyl)-2-propenenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

Trifluoroacetic acid (600 ml) was slowly added to the residue of 2,6-dimethyl-4-(2-cyanoethenyl)-1-carboxybenzyl phenylamine obtained from example 2 (161 gms) at 25 to 30° C. and the reaction mass was stirred at 45-60° C. till completion of reaction as monitored by TLC. After completion of the reaction, water (1800 ml) was added to the reaction mass, neutralized with aqueous ammonia and extracted with toluene. The organic layer was separated and concentrated to give 2,6-dimethyl-4-(2-cyanoethenyl)phenylamine. The residue was admixed with 1:1 mixture of isopropanol and diisopropyl ether (1000 ml) and treated with HCl dissolved in isopropanol to yield 2,6-dimethyl-4-(2-cyanoethenyl)phenylamine hydrochloride salt (II) which was cooled to 25-30° C., filtered and dried.

Workup

  1. additionwas added to the reaction mass
  2. extractionextracted with toluene
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab988fd451db40eead838371203d72f4
Source dataset
uspto-grants-2015_02
Patent number
US08952155B2

Reaction notes

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