2,6-Dimethylaniline → 4-Amino-N-(2,6-dimethylphenyl)phthalimide

HRID 2402520

Reaction equation

HRID 2402520 reaction equation
[N+:1]([C:4]1[CH:14]=[C:8]2[C:9]([O:11][C:12](=[O:13])[C:7]2=[CH:6][CH:5]=1)=O)([O-])=O.[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=1[NH2:18].[Sn](Cl)Cl.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[NH2:1][C:4]1[CH:14]=[C:8]2[C:7](=[CH:6][CH:5]=1)[C:12](=[O:13])[N:18]([C:17]1[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:16]=1[CH3:15])[C:9]2=[O:11]

Participants

7

Reactant 4

HCID 68962,6-DimethylanilineHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 1240314-Amino-N-(2,6-dimethylphenyl)phthalimideYield 67.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 5-nitrophthalic anhydride (1.0 g, 5.2 mmol) and 2,6-dimethylaniline (0.65 mL, 5.3 mmol) in acetic acid (50 mL) was heated at 100° C. overnight (14 h). The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The product was dissolved in ethanol (50 mL), tin (II) chloride (1.4 g, 6.2 mmol) was added and the mixture was heated to reflux for 5 h. The reaction mixture was cooled and made basic by adding aqueous 2 N sodium hydroxide. Ethyl acetate was added and the layers were separated. The organic layer was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to give 5-amino-2-(2,6-dimethylphenyl)isoindoline-1,3-dione (0.93 g, 67%), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe product was dissolved in ethanol (50 mL)
  7. temperaturethe mixture was heated
  8. temperatureto reflux for 5 h
  9. temperatureThe reaction mixture was cooled
  10. customthe layers were separated
  11. washThe organic layer was washed with water and saturated sodium chloride
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-cf9aaa88b74e4573b5c46299e5a1e6ea
Source dataset
uspto-grants-2014_08
Patent number
US08796294B2

Linked notes

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