Water → HCID 21463132, compound

HRID 375005Notes

Reaction equation

HRID 375005 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 altered off. The filtrate 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-phenylquinolin 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. washThe filtrate was washed by successively with aqueous potassium carbonate and saturated aqueous sodium chloride
  4. customdried
  5. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-d295639396e64b2185f8df6d42063a2e
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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