3-(Trifluoromethyl)aniline → HCID 178459327, compound

HRID 1895096Notes

Reaction equation

HRID 1895096 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-40078a769c8d44a183c0d77f94e19743
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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