3-(Trifluoromethyl)aniline → HCID 178459327, compound

HRID 1624569Notes

Reaction equation

HRID 1624569 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N:12]([O-])=O.[Na+].[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])(=[O:19])[CH2:17][CH3:18].C([O-])(=O)C.[Na+]>Cl.O.C(O)C>[O:19]=[C:16]([CH2:17][CH3:18])[C:20](=[N:12][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

8

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 121699Methyl 3-oxovalerateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178459327HCID 178459327, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of 3-(trifluoromethyl)aniline (8.03 g, 50 mmol) in 6 N HCl (50 mL) was cooled to 0° C. and treated dropwise with a solution of sodium nitrite (4.10 g, 60 mmol) in water (10 mL). The resulting pale yellow solution was poured into a suspension of methyl propionylacetate (6.50 g, 50 mmol) and sodium acetate (24.00 g, 292 mmol) in ethanol (80 mL), pre-cooled to 0° C. The resulting yellow/orange slurry was stirred for 30 min. The product was collected by filtration and washed with water (100 mL). The crude material was dissolved in ethyl acetate (100 mL) and dried (Na2SO4). The product crystallized upon concentration of the ethyl acetate to give (14.00 g, 93%) of methyl 3-oxo-2-{[3-(trifluoromethyl)phenyl]hydrazono}pentanoate as a yellow/orange solid.

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed with water (100 mL)
  3. dissolutionThe crude material was dissolved in ethyl acetate (100 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe product crystallized upon concentration of the ethyl acetate

Sources & evidence

ORD record
ord-c69a6ab471274e728dbc85b6734dc4b1
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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