Ethanol → 5-Ethoxy-2-nitro-4-(trifluoromethyl)aniline

HRID 418143Notes

Reaction equation

HRID 418143 reaction equation
[CH3:1][CH2:2][OH:3].[K].Cl[C:6]1[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([NH2:12])[CH:11]=1>O>[CH2:2]([O:3][C:6]1[C:7]([C:16]([F:17])([F:19])[F:18])=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([NH2:12])[CH:11]=1)[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 27738135-Chloro-2-nitro-4-(trifluoromethyl)anilineHCID 5462222Potassium2×

Product 1

HCID 223171555-Ethoxy-2-nitro-4-(trifluoromethyl)anilineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To EtOH (500 mL) was added potassium metal (ca. 21 g, ca. 537 mmol) and the vigorous reaction had to be cooled with an ice bath. Stirring was continued until all potassium metal was dissolved. Solid commercially available 5-chloro-2-nitro-4-trifluoromethyl-phenylamine [CAS-No. 35375-74-7] (57.74 g, 240 mmol) was added in one portion and the resulting dark red mixture was stirred at 55-60° C. for 4 days. The warm reaction mixture was slowly poured into H2O (ca. 2000 mL), adjusted pH with conc. HC1 to pH 2, the yellow precipitate was filtered off, washed with H2O and dried in air at 60° C. to give a yellow solid (57.81 g, 96%), which was used without further purification. MS (ISN) 249 [M−H].

Workup

  1. customthe vigorous reaction
  2. temperatureto be cooled with an ice bath
  3. dissolutionwas dissolved
  4. stirringthe resulting dark red mixture was stirred at 55-60° C. for 4 days
  5. customThe warm reaction mixture
  6. filtrationto pH 2, the yellow precipitate was filtered off
  7. washwashed with H2O
  8. customdried in air at 60° C.

Sources & evidence

ORD record
ord-1ce9944de14e496a852d5953a5f641f3
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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