Propionic Acid → 2-Ethylthiazolo[4,5-c]quinoline

HRID 1168746Notes

Reaction equation

HRID 1168746 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[SH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:13](O)(=O)[CH2:14][CH3:15]>>[CH2:14]([C:15]1[S:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:13]

Participants

3

Reactant 2

HCID 1032Propionic AcidHCID 1785079903-Aminoquinoline-4-thiol

Product 1

HCID 150279042-Ethylthiazolo[4,5-c]quinoline

Procedure

Propionyl anhydride (20 mL) was added to a suspension of 3-amino-quinoline-4-thiol (15 g) in propionic acid (100 mL). The reaction mixture was heated at reflux overnight and then filtered to remove a precipitate. The filtrate was concentrated under vacuum. The residue was taken up in dichloromethane (200 mL), washed with sodium bicarbonate then with water, and then dried over magnesium sulfate. The solution was filtered through a layer of silica gel eluting first with 1:1 ethyl acetate:hexane and then with ethyl acetate. The filtrate was evaporated to provide 2.6 g of 2-ethylthiazolo[4,5-c]quinoline as a yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. customto remove a precipitate
  5. concentrationThe filtrate was concentrated under vacuum
  6. washwashed with sodium bicarbonate
  7. dry with materialwith water, and then dried over magnesium sulfate
  8. filtrationThe solution was filtered through a layer of silica gel eluting first with 1:1 ethyl acetate
  9. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-4e707f5d37cf4418bdb2d4b1946eb3ae
Source dataset
uspto-grants-2003_09
Patent number
US06627638B2

Reaction notes

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