Diethyl Ether → HCID 178437756, compound

HRID 1415710Notes

Reaction equation

HRID 1415710 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.[C:16]1(C)[CH:21]=CC(S(O)(=O)=O)=C[CH:17]=1.C(OCC)C>C(OCC)(OCC)(OCC)CC>[CH2:16]([C:21]1[NH:1][C:2]2=[N:3][C:4]3[C:9]([CH:10]=[C:11]2[C:12](=[O:13])[N:14]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH3:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 52002282-Amino-3-quinolinecarboxamide

Product 1

HCID 178437756HCID 178437756, compoundYield 236.5%

Reagents, catalysts & solvents 1

HCID 66995Ethyl orthopropionateSolvent

Procedure

A slurry of 2-aminoquinoline-3-carboxamide (1.0 g, 5.3 mmol), (Campaigne, E.; Randau, G. J. Het. Chem. 1971, Vol. 8, p. 111) and p-toluenesulfonic acid-monohydrate (50 mg) in triethyl orthopropionate (25 mL) was refluxed for 24 hours. After cooling, the reaction mixture was diluted into diethyl ether (50 mL), the resulting solids filtered and washed with diethyl ether. The solids were recrystallized from formamide to afford 0.14 g of the title compound; m.p. 240-245° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting solids filtered
  3. washwashed with diethyl ether
  4. customThe solids were recrystallized from formamide

Sources & evidence

ORD record
ord-77e6701bec1f45ec93bb900ec1b7b13e
Source dataset
uspto-grants-1999_06
Patent number
US05908930

Reaction notes

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