Isoamyl Nitrite → N-(3-Methoxy-2,4,5-trifluorophenyl)-phthalimide

HRID 358870Notes

Reaction equation

HRID 358870 reaction equation
[CH3:1][O:2][C:3]1[C:9]([F:10])=[C:8]([F:11])[C:6](N)=[C:5]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[C:4]=1[F:23].N(OCCC(C)C)=O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([F:23])=[C:5]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH:6]=[C:8]([F:11])[C:9]=1[F:10]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 200671534-Methoxy-2-phthalimido-3,5,6-trifluoroaniline

Product 1

HCID 20067133N-(3-Methoxy-2,4,5-trifluorophenyl)-phthalimideYield 78.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.90 g (0.009 mole) of 4-methoxy-2-phthalimido-3,5,6-trifluoroaniline (XXXV) [prepared as described in Step (F2) above] in 18 ml of dimethylformamide was added dropwise, whilst stirring at 60°-65° C., to a solution of 1.66 g (0.0144 mole) of isoamyl nitrite in 9 ml of dimethylformamide. After the addition was complete, the reaction mixture was stirred at the same temperature for 1 hour, and then the solvent was removed by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography eluted with toluene, to afford 2.18 g of N-(3-methoxy-2,4,5-trifluorophenyl)phthalimide (XXXVI) as colorless powdery crystals.

Workup

  1. additionAfter the addition
  2. customthe solvent was removed by evaporation under reduced pressure
  3. washeluted with toluene

Sources & evidence

ORD record
ord-7e122c9dae6d4d67ab57e77cb1425873
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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