Succinic anhydride → HCID 86743814, compound

HRID 1165681Notes

Reaction equation

HRID 1165681 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[OH-].[NH4+:9]>CN1C(=O)CCC1>[C:1]([O-:6])(=[O:7])[CH2:2][CH2:3][C:4]([NH2:9])=[O:5].[NH4+:9]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 14923Ammonium Hydroxide

Product 1

HCID 86743814HCID 86743814, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To demonstrate that the reactions involved above are, in fact, clean and very nearly quantitative as claimed, the experiments described below were carried out. Succinic anhydride (10 g.; 0.1 mole) was dissolved with magnetic stirring in NMP (100 ml.). Conc. ammonium hydroxide (15 ml; 0.225 mole) was added dropwise with stirring. After the addition, the stirring was continued for 3 hours, and the product precipitated during this period. The mixture was cooled, stirring was continued, and ether (100 ml.) was added dropwise. This was done to ensure complete precipitation of the product. The reaction was refrigerated overnight and on filtration yields 13.4 g (100% yield) of ammonium succinamate; m.p., 112°-120°. A sample recrystallized from methanol had m.p., 108°-118°. Anal: for ammonium succinate C4H10N2O3 : calc. N, 20.88%; found N, 20.38%, 20.30%.

Workup

  1. additionAfter the addition
  2. customthe product precipitated during this period
  3. temperatureThe mixture was cooled
  4. stirringstirring
  5. additionether (100 ml.) was added dropwise
  6. customprecipitation of the product
  7. filtrationThe reaction was refrigerated overnight and on filtration

Sources & evidence

ORD record
ord-1319944f0f434b9abf5da65bb098a9fb
Source dataset
uspto-grants-1990_03
Patent number
US04910644

Reaction notes

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