Methanol → HCID 531812, compound

HRID 1800477Notes

Reaction equation

HRID 1800477 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].CO>N1C=CC=CC=1.CN(C)C1C=CN=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

6

Reactant 3

HCID 887MethanolHCID 74233-NitroanilineHCID 752573-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 531812HCID 531812, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 3-nitroaniline (13.8 g, 99.9 mmol) in pyridine (200 mL) were added 3-(trifluoromethyl)benzoyl chloride (21.4 g, 103 mmol) and N,N-dimethylpyridine-4-amine (69.1 mg, 566 μmol), and the mixture was stirred at room temperature for 1.5 hr. Methanol (50 mL) was added to the reaction solution to stop the reaction, and the solvent was evaporated under reduced pressure. The residue was suspended in ethyl acetate (300 mL), washed with water (200 mL×2), 0.1N 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
  2. customthe solvent was evaporated under reduced pressure
  3. washwashed with water (200 mL×2), 0.1N 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-d1cae85f73ae45a185f15b3d50d446b4
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…