Ammonium Acetate → 4-Fluoro-2-methyl-5-phthalimidoindole

HRID 2222427Notes

Reaction equation

HRID 2222427 reaction equation
[C:1]([CH2:4][C:5]1[C:10]([F:11])=[C:9]([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:8]=[CH:7][C:6]=1[N+:23]([O-])=O)(=O)[CH3:2].C([O-])(=O)C.[NH4+]>CC(C)=O.[Cl-].[Cl-].[Cl-].[Ti+3]>[F:11][C:10]1[C:9]([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:8][CH:7]=[C:6]2[C:5]=1[CH:4]=[C:1]([CH3:2])[NH:23]2

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 591066072-(Acetylmethyl)-3-fluoro-4-phthalimidonitrobenzene

Product 1

HCID 597122384-Fluoro-2-methyl-5-phthalimidoindoleYield 31%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 180AcetoneSolvent

Procedure

2-(Acetylmethyl)-3-fluoro-4-phthalimidonitrobenzene (4.7 g, 14 mmol) was dissolved in acetone (80 ml). Ammonium acetate (210 ml of a freshly prepared 4M aqueous solution) was added followed by titanium trichloride (140 ml, 140 mmol, 15% aqueous solution). The mixture was stirred vigorously for 30 minutes then extracted with ethyl acetate. The organic phase was washed with a hydrogen carbonate solution, brine, dried (MgSO4), filtered and the solvent evaporated off. The residue was purified by flash chromatography using 0.5% methanol in methylene chloride. Evaporation of the solvent gave 4-fluoro-2-methyl-5-phthalimidoindole (1.27 g; 31%).

Workup

  1. extractionthen extracted with ethyl acetate
  2. washThe organic phase was washed with a hydrogen carbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated off
  6. customThe residue was purified by flash chromatography
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a355dbec5c954d0089d3f7b2b1c83288
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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