2-Methyl-8-hydroxyquinoline → HCID 13338829, compound

HRID 2418222Notes

Reaction equation

HRID 2418222 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]=[O:15]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C(C(C)=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][C:14]([NH:13][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 132242-Methyl-8-hydroxyquinolineHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 13338829HCID 13338829, compound

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 15.9 g of 2-methyl-8-hydroxyquinoline, 13.6 g of ethyl isocyanatoacetate and 10 drops of dibutyltin dilaurate in 200 ml of methyl ethyl ketone was heated at reflux temperature for seven hours, after which the solvent was removed by evaporation in vacuo leaving a solid residue. The residue was recrystallized from toluene to give the desired ethyl N-(((2-methyl-8-quinolinyl)oxy)carbonyl)glycinate as light tan crystals, m.p. 118°-120° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for seven hours
  3. customafter which the solvent was removed by evaporation in vacuo
  4. customleaving a solid residue
  5. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-8a5a0ae1424a4e37982571e92eaef881
Source dataset
uspto-grants-1984_09
Patent number
US04472404

Reaction notes

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