Water → HCID 21463132, compound

HRID 1940973Notes

Reaction equation

HRID 1940973 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=O.C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)(=O)C>[Cl:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]=[CH:6][C:5]([CH2:3][OH:2])=[C:14]2[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 10447368HCID 10447368, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21463132HCID 21463132, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While stirring a mixture of 6-chloro-4-phenyl-3-quinolinecarboxylic acid methyl ester (8.0 g) and ethyl ether (100 ml) at 0° C., lithium aluminum hydride (1.0 g) was added, followed by stirring for 30 minutes. After water (5 ml) was added, the mixture was stirred at room temperature for 30 more minutes. After ethyl acetate was added; the insoluble material was filtered off. The flitrate was washed by successively with aqueous potassium carbonate and saturated aqueous sodium chloride and then dried, after which the solvent was distilled off, to yield 6-chloro-3-hydroxymethyl-4-phenylquinoline as colorless crystals (6.05 g).

Workup

  1. stirringby stirring for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 30 more minutes
  3. filtrationthe insoluble material was filtered off
  4. washThe flitrate was washed by successively with aqueous potassium carbonate and saturated aqueous sodium chloride
  5. customdried
  6. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-adaca68dcf364e4f998bbd2990de10ec
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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