Ethyl Acetate → 2-Chloro-4-nitro-6-(trifluoromethyl)aniline

HRID 1820133Notes

Reaction equation

HRID 1820133 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)([O-:3])=[O:2].[Cl:15]N1C(=O)CCC1=O.[OH-].[Na+].C(OC(=O)C)C>C(#N)C>[Cl:15][C:9]1[CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:11]([F:12])([F:13])[F:14])[C:7]=1[NH2:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidine

Product 1

HCID 137844272-Chloro-4-nitro-6-(trifluoromethyl)anilineYield 97.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

4-Nitro-2-trifluoromethylaniline (15 g) and N-chlorosuccinimide (10.7 g) dissolved in acetonitril (100 ml) was heated to 150° C. for 15 minutes in a sealed microwave process vial. The reaction mixture was cooled to ambient temperature and poured into 5% sodium hydroxide (500 ml) and ethylacetate (400 ml). After seperation the organic phase was dried (MgSO4), filtered and concentrated in vacuo, followed by purification by flash chromatography to furnish 17.0 g (97% yield) of the title compound as a yellow solid. LC-MS (m/z) 240 (MH+); tR=4.76, (UV, ELSD) 97%, 96%. 1H NMR (500 MHz, DMSO-d6): 7.15 (s, 2H), 8.15 (d, 1H), 8.40 (d, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customAfter seperation the organic phase
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customfollowed by purification by flash chromatography

Sources & evidence

ORD record
ord-75467a2a5afb462281c4289cb8c90851
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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