Carbon Dioxide → HCID 178498476, compound

HRID 1494305Notes

Reaction equation

HRID 1494305 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=1.[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([S:22]([N:25]=C=O)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)=O>C(#N)C>[C:16]1([CH3:28])[CH:17]=[CH:18][C:19]([S:22]([N:25]=[C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]([C:12]([O:14][CH3:15])=[O:13])=[CH:3]2)(=[O:23])=[O:24])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 77703p-Toluenesulfonyl isocyanateHCID 178498498HCID 178498498, compound

Product 1

HCID 178498476HCID 178498476, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to the procedure of Wright, Synthesis, 1984, 1058, methyl 4-hydroxy-2-quinolinecarboxylate (2.03 g, 0.01 m) and p-toluenesulfonyl isocyanate (1.97 g, 0.01 m) were mixed in reagent grade acetonitrile at RT. The heterogeneous mixture was heated at reflux until the evolution of CO2 had ceased (ca 2-3 hours). During this time a yellow solid formed. After cooling to RT, the yellow solid was collected by filtration, washed with acetonitrile, and dried to give methyl 4-(p-toluenesulfonylimino)-1,4-dihydroquinoline-2-carboxylate (2.93 g, 82%), melting point of 264°-265° C. (dec.), as a yellow solid.

Workup

  1. temperatureThe heterogeneous mixture was heated
  2. custom(ca 2-3 hours)
  3. customDuring this time a yellow solid formed
  4. filtrationthe yellow solid was collected by filtration
  5. washwashed with acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-8da74b8e13c84ebb8f41d459f089f4f4
Source dataset
uspto-grants-1991_06
Patent number
US05026700

Reaction notes

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