p-Toluenesulfonic acid → HCID 13730722, compound

HRID 980529Notes

Reaction equation

HRID 980529 reaction equation
[C:1]([C:3]([N:8]1[C:12](=[O:13])[CH:11]=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:21]=O)[C:9]1=[O:23])([CH3:7])[CH:4]([CH3:6])[CH3:5])#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH:4]([C:3]([CH3:7])([N:8]1[C:12](=[O:13])[C:11]2[C:10](=[N:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH:21]=2)[C:9]1=[O:23])[C:1]#[N:2])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13730723HCID 13730723, compound

Product 1

HCID 13730722HCID 13730722, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of N-(1-cyano-1,2-dimethylpropyl)-2-(o-formylanilino)maleimide (7.19 g, 0.023 mol) in xylene (300 ml) containing p-toluenesulfonic acid (0.3 g, 0.0016 mol) is heated at reflux for 4 hours using a Dean-Stark trap to collect the eliminated water. The reaction is cooled, evaporated under reduced pressure and dissolved in hot ethyl acetate which is passed through a 3 inch silica gel column. The ethyl acetate fractions eluted are combined to give a solid, mp 195°-195.5° C., 5.51 g, (81%) of 1,3-dihydro-α-isopropyl-α-methyl-1,3-dioxo-2-H-pyrrolo[3,4-b]quinoline-2-acetonitrile.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. customto collect the eliminated water
  4. temperatureThe reaction is cooled
  5. customevaporated under reduced pressure
  6. dissolutiondissolved in hot ethyl acetate which
  7. washThe ethyl acetate fractions eluted

Sources & evidence

ORD record
ord-b391b3b63385434c85f0f851487a29c0
Source dataset
uspto-grants-1987_01
Patent number
US04638068

Reaction notes

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