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

HRID 542259Notes

Reaction equation

HRID 542259 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-527cd2f6b0cb4cee8e74260abb0b8db8
Source dataset
uspto-grants-1987_04
Patent number
US04656281

Reaction notes

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