Phthalic Anhydride → Ammonium 2-(aminocarbonyl)benzoate

HRID 1077679

Reaction equation

HRID 1077679 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C([NH2:16])CCC>ClCCl>[C:1]([O-:6])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([NH2:16])=[O:5].[NH4+:16]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 8007Butylamine

Product 1

HCID 3083555Ammonium 2-(aminocarbonyl)benzoateYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A heterogenous mixture of phthalic anhydride (10.0 g, 67.5 mmol) and 100 mL of dichloromethane was cooled in an ice bath. n-Butyl amine (12.345 g, 168.78 mmol) was added dropwise. The temperature was not allowed to rise above 15° C. during the addition. When a small amount of the amine had been added a homogenous solution resulted. After a short time, a white precipitate formed. As more amine was added, the precipitate redissolved and a solution again formed. Upon completion of the addition the reaction was allowed to stir in an ice bath for 10 minutes. A white precipitate again formed. The mixture was allowed to stir at 0° C. for 50 minutes and at room temperature for 10 minutes. The precipitate was filtered off and washed with a small amount of dichloromethane. Washing with hexanes and drying in air afforded 8.86 g of compound AM-1. NMR was in agreement with the proposed structure.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionto rise above 15° C. during the addition
  3. customresulted
  4. customAfter a short time, a white precipitate formed
  5. dissolutionthe precipitate redissolved
  6. customa solution again formed
  7. additionUpon completion of the addition the reaction
  8. customA white precipitate again formed
  9. stirringto stir at 0° C. for 50 minutes and at room temperature for 10 minutes
  10. filtrationThe precipitate was filtered off
  11. washwashed with a small amount of dichloromethane
  12. washWashing with hexanes
  13. customdrying in air

Sources & evidence

ORD record
ord-684655c60de84e89bb53f129a486d98c
Source dataset
uspto-grants-1996_08
Patent number
US05545505

Linked notes

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