Sodium Carbonate → 4-amino-N-butylphthalimide

HRID 1633958

Reaction equation

HRID 1633958 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2=[CH:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=[C:7]2[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=[C:7]2[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 932972-Butyl-5-nitro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 3289774-amino-N-butylphthalimideYield 59.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of N-butyl-4-nitrophthalimide (1.45 g, 5.8 mmol) in methanol (30 mL) was added drop wise to a well stirred solution of sodium dithionite (6.50 g, 37.1 mmol) and sodium carbonate (3.22 g, 30.5 mmol) in water (40 mL), while the temperature was maintained at 70° C. After addition, heating at 70° C. was continued for a further 30 minutes, then the reaction mixture was allowed to cool to room temperature. The reaction volume was reduced to one third by rotary evaporation, and the residual water solution was extracted with diethyl ether (2×50 mL). The combined organic phases were dried with anhydrous Na2SO4, and then taken to dryness. The residual oil was recrystallised from ethanol/water to give 750 mg (59%) of N-butyl-4-aminophthalimide.

Workup

  1. additionAfter addition
  2. temperatureheating at 70° C.
  3. temperatureto cool to room temperature
  4. customThe reaction volume was reduced to one third by rotary evaporation
  5. extractionthe residual water solution was extracted with diethyl ether (2×50 mL)
  6. dry with materialThe combined organic phases were dried with anhydrous Na2SO4
  7. customThe residual oil was recrystallised from ethanol/water

Sources & evidence

ORD record
ord-59cb9c93e6c0454e980d30d7a40fad3a
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Linked notes

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