Ethanol → HCID 178507996, compound

HRID 1872648Notes

Reaction equation

HRID 1872648 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:15])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.C(O)C.C(=O)(O)[O-].[Na+]>O>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[OH:15])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2

Participants

6

Reactant 4

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 178526772HCID 178526772, compound

Product 1

HCID 178507996HCID 178507996, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-Chloro-3-nitro-4-hydroxyquinoline (4.48 g, 20 mmol), tin (II) chloride dihydrate (22.6 g, 100 mmol) and ethanol (200 mL) were combined and then heated at reflux for 4 hours. The reaction mixture was cooled to ambient temperature and then poured into water (250 mL). The mixture was brought to neutral pH by the addition of saturated sodium bicarbonate and then filtered to remove tin salts. The filtrate was extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered and then concentrated under vacuum to provide 1.8 g of 3-amino-7-chloro-4-hydroxyquinoline as a green powder.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. customto remove tin salts
  5. extractionThe filtrate was extracted with ethyl acetate
  6. dry with materialThe combined organic fractions were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-eb84b67e86454c27b7ee5322ef61f2fa
Source dataset
uspto-grants-2000_08
Patent number
US06110929

Reaction notes

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