Phthalic Anhydride → N-(cyano-1,2-dimethylpropyl)phthalamic acid

HRID 372352

Reaction equation

HRID 372352 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.[NH2:12][C:13]([CH3:19])([CH:16]([CH3:18])[CH3:17])[C:14]#[N:15]>C(Cl)Cl>[C:14]([C:13]([NH:12][C:4](=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:1]([OH:6])=[O:11])([CH3:19])[CH:16]([CH3:18])[CH3:17])#[N:15]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 943552-Amino-2,3-dimethylbutyronitrile

Product 1

HCID 4890749N-(cyano-1,2-dimethylpropyl)phthalamic acidYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred boiling mixture of 28.1 g (0.189 mole) of phthalic anhydride in 28 ml methylene chloride is added dropwise 23.6 g (0.21 mole) of 2-amino-2,3-dimethylbutyronitrile in 57 ml methylene chloride. After the addition, heating is continued for 3 hours. The mixture is cooled and the precipitate removed by filtration, washed with methylene chloride and air-dried to give 44.2 g (90%) of N-(1-cyano-1,2-dimethylpropyl)phthalamic acid, melting point 154°-155° C.

Workup

  1. additionAfter the addition
  2. temperatureheating
  3. temperatureThe mixture is cooled
  4. customthe precipitate removed by filtration
  5. washwashed with methylene chloride
  6. customair-dried

Sources & evidence

ORD record
ord-29905e1b2a6e4b5b90a4b49a2771dcd9
Source dataset
uspto-grants-1978_05
Patent number
US04090860

Linked notes

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