Water → HCID 178519811, compound

HRID 1915009Notes

Reaction equation

HRID 1915009 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16](OCC)=[O:17].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:13])[F:14])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178469560HCID 178469560, compound

Product 1

HCID 178519811HCID 178519811, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14 grams (50 mmol) of ethyl 4-hydroxy-7-trifluoromethyl-3-quinolinecarboxylate was suspended in 400 ml THF, and 9.5 grams (250 mmol) lithium aluminum hydride were added slowly. The mixture was stirred at room temperature for 12 hours, cooled, 250 ml water was added and the resulting mixture was stirred overnight. The solvent was thereafter evaporated, and water (300 ml) was again added. The aqueous suspension was extracted with dichloromethane. The organic extract was evaporated, and the remaining residue was purified by column chromatography on silica gel, using a 9:1 mixture of ethylacetate and methanol as eluent, to yield 4-hydroxy-7-trifluoromethyl-3-(hydroxymethyl)-quinoline (12 grams, 82% yield).

Workup

  1. temperaturecooled
  2. stirringthe resulting mixture was stirred overnight
  3. customThe solvent was thereafter evaporated
  4. additionwater (300 ml) was again added
  5. extractionThe aqueous suspension was extracted with dichloromethane
  6. extractionThe organic extract
  7. customwas evaporated
  8. customthe remaining residue was purified by column chromatography on silica gel
  9. additiona 9:1 mixture of ethylacetate and methanol as eluent

Sources & evidence

ORD record
ord-5813cf549cf141edabb34c8221ce82cf
Source dataset
uspto-grants-2013_12
Patent number
US08614319B2

Reaction notes

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