Sulfuric Acid → Succinanilic acid

HRID 1597751

Reaction equation

HRID 1597751 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O>C(#N)C>[C:10]1([NH:9][C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6115AnilineHCID 138186494-Chloro-4-oxobutanoic acid

Product 1

HCID 7598Succinanilic acidYield 63.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 mg of succinic acid monochloride are dissolved in 2 ml of anhydrous acetonitrile. 1.5 equivalents of aniline (102 mg) are added at room temperature and the reaction mixture is kept stirred for 30 minutes. 100 ml of 0.005M sulfuric acid are then added and the solution is extracted with ethyl ether (3×3 ml). The ether phases are combined and washed with water to neutrality and then dried over anhydrous MgSO4. The ether is then filtered and evaporated under reduced pressure to give 90 mg of N-phenylsuccinamic acid.

Workup

  1. extractionthe solution is extracted with ethyl ether (3×3 ml)
  2. washwashed with water to neutrality
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationThe ether is then filtered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0e8803e23b8d43e593af33fb4f713637
Source dataset
uspto-grants-1998_04
Patent number
US05736371

Linked notes

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