3-Nitroaniline → HCID 531812, compound

HRID 1800663Notes

Reaction equation

HRID 1800663 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([C:12]([F:11])([F:22])[F:23])[CH:14]=2)[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74233-NitroanilineHCID 752573-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 531812HCID 531812, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-nitroaniline(13.8 g, 99.9 mmol) in pyridine (200 mL) were added 3-(trifluoromethyl)benzoylchloride (21.4 g, 103 mmol) and N,N-dimethylaminopyridine (69.1 mg, 566 μmol), and the mixture was stirred at room temperature for 1.5 hr. The reaction was quenched with methanol (50 mL), and the solvent was evaporated under reduced pressure. The residue was suspended in ethyl acetate (300 mL), washed with water (200 mL×2), diluted hydrochloric acid (200 mL×2), saturated aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (100 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (31.0 g, 100%) as a colorless solid.

Workup

  1. customThe reaction was quenched with methanol (50 mL)
  2. customthe solvent was evaporated under reduced pressure
  3. washwashed with water (200 mL×2), diluted hydrochloric acid (200 mL×2), saturated aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-09d403ff44954741beed513f0f36c6eb
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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