Ammonia → HCID 59488742, compound

HRID 561186Notes

Reaction equation

HRID 561186 reaction equation
C(O[CH:4]=[CH:5][C:6](O)([C:16]([F:19])([F:18])[F:17])[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9])C.[NH3:21]>>[C:10]1([C:7]2[C:8]([NH2:9])=[N:21][CH:4]=[CH:5][C:6]=2[C:16]([F:19])([F:18])[F:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 66998207HCID 66998207, compound

Product 1

HCID 59488742HCID 59488742, compoundYield 57.7%

Conditions

Temperature
125 °C

Procedure

50 g of 5-ethoxy-3-hydroxy-2-phenyl-3-trifluoromethylpent-4-enenitrile were mixed with 600 g of aqueous ammonia (25%), and the resulting mixture was heated to 125° C. in an autoclave for 24 h. Subsequently, the reaction mixture was cooled and the resulting biphasic mixture was extracted repeatedly with dichloromethane. The combined organic phases were concentrated by rotary evaporation and the product was subsequently recrystallized from heptane. 24.1 g of 3-phenyl-4-trifluoromethylpyridin-2-ylamine (52% over both stages) were thus isolated.

Workup

  1. temperatureSubsequently, the reaction mixture was cooled
  2. extractionthe resulting biphasic mixture was extracted repeatedly with dichloromethane
  3. concentrationThe combined organic phases were concentrated by rotary evaporation
  4. customthe product was subsequently recrystallized from heptane

Sources & evidence

ORD record
ord-a56038ff434a4975a710cb861d83cb05
Source dataset
uspto-grants-2011_11
Patent number
US08063226B2

Reaction notes

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