Acetic Acid → HCID 13285985, compound

HRID 1903895Notes

Reaction equation

HRID 1903895 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.C(O)(=O)C.[C:16]([CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[Cl:27])[NH2:23])#[N:17]>O>[C:16]([CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([N:23]2[C:1](=[O:11])[C:2]3[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=3[C:4]2=[O:6])[CH:24]=[CH:25][C:26]=1[Cl:27])#[N:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 132859845-Amino-2-chlorobenzenepropanenitrile

Product 1

HCID 13285985HCID 13285985, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred slurry of 5.0 g of 3,4,5,6-tetrahydrophthalic anhydride in 5 ml. of glacial acetic acid under N2 is added 7.5 g of 3-(2-cyanoethyl)-4-chloroaniline and the mixture heated to reflux for 2 hours. The reaction mixture is cooled to room temperature, water is added together with several mls. of conc. HCl and the mixture extracted with ether. The combined ether extracts are washed with saturated brine and then dried over MgSO4. Filtration and removal of the solvent yielded 8.9 g of a brown oil. The oil is dissolved in CH2Cl2, passed through a plug of alumina, the solvent removed, and then further purified by MPLC eluting with 25% EtOAc/hexanes to yield the product as a yellow solid, m.p. 87°-97° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. extractionof conc. HCl and the mixture extracted with ether
  4. washThe combined ether extracts are washed with saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and removal of the solvent

Sources & evidence

ORD record
ord-a9582eacf9cd47f595008e63f2c5e554
Source dataset
uspto-grants-1984_03
Patent number
US04439229

Reaction notes

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