3-(Trifluoromethyl)aniline → HCID 178501727, compound

HRID 1407075Notes

Reaction equation

HRID 1407075 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]([O:22][CH3:23])(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19].C([O-])(=O)C.[Na+]>Cl.O.C(O)C>[O:19]=[C:18]([CH3:20])[C:17](=[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:16]([O:22][CH3:23])=[O:21]

Participants

8

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 7757Methyl acetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178501727HCID 178501727, compoundYield 69.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of 3-(trifluoromethyl)aniline (16.12 g, 100 mmol) in 6 N HCl (100 mL) was cooled to 0° C. and treated dropwise with a solution of sodium nitrite (8.33 g, 121 mmol) in water (20 mL). The resulting pale yellow solution was poured into a slurry of methyl acetoacetate (11.62 g, 100 mmol) and sodium acetate (150 g) in ethanol (170 mL), pre-cooled to 0° C. The resulting orange slurry was stirred for 10 min. After that time, the product was collected by filtration and washed with water (500 mL). The crude material was dissolved in ethyl acetate (250 mL) and dried (MgSO4). The product crystallized upon concentration of the ethyl acetate to give 19.997 g (69%) of methyl 3-oxo-2-{[3-(trifluoromethyl)phenyl]hydrazono}butanoate as light yellow crystals.

Workup

  1. filtrationAfter that time, the product was collected by filtration
  2. washwashed with water (500 mL)
  3. dissolutionThe crude material was dissolved in ethyl acetate (250 mL)
  4. dry with materialdried (MgSO4)
  5. customThe product crystallized upon concentration of the ethyl acetate

Sources & evidence

ORD record
ord-9d83eef5c4f341579589f6ef34e28cdc
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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