Ethanol → HCID 178507996, compound

HRID 48300Notes

Reaction equation

HRID 48300 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-763fb7c7fde943fea80e326077b9fa2c
Source dataset
uspto-grants-2004_03
Patent number
US06703402B2

Reaction notes

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