7-Amino-5-chloroquinolin-8-ol → Quazolast

HRID 1248166Notes

Reaction equation

HRID 1248166 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([NH2:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:14][O:15][C:16](OC)([O:21]C)[C:17](OC)=O>>[C:16]([C:17]1[O:13][C:9]2[C:8]3[N:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:2]([Cl:1])=[CH:11][C:10]=2[N:12]=1)([O:15][CH3:14])=[O:21]

Participants

3

Reactant 2

HCID 4174907-Amino-5-chloroquinolin-8-olHCID 12586559Methyl 2,2,2-trimethoxyacetate

Product 1

HCID 24747QuazolastYield 51%

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-7-amino-8-hydroxyquinoline (6 g, 30.8 mol) and methyl trimethoxyacetate (16.3 g, 123.2 mol) was heated at 100° C. overnight. The reaction was cooled in an ice bath and filtered. The precipitate was dissolved in acetone (250 ml). The resulting solution was treated with charcoal at reflux, filtered through a pad of silica gel and celite and partially concentrated. Crystals formed which were filtered and dried giving 4.1 g (51% yield) of solid. M.P. 217°-218° C.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. filtrationfiltered
  3. dissolutionThe precipitate was dissolved in acetone (250 ml)
  4. additionThe resulting solution was treated with charcoal
  5. temperatureat reflux
  6. filtrationfiltered through a pad of silica gel and celite
  7. concentrationpartially concentrated
  8. customCrystals formed which
  9. filtrationwere filtered
  10. customdried

Sources & evidence

ORD record
ord-a3d3feec029d43bf9fa43ea2e361bb4f
Source dataset
uspto-grants-1985_06
Patent number
US04522947

Reaction notes

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