Sodium borohydride → HCID 67690574, compound

HRID 1940967Notes

Reaction equation

HRID 1940967 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])=[CH:13][C:12]([CH3:23])=[C:11]([CH3:24])[CH:10]=2)=[O:5])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:14]2[C:9](=[CH:10][C:11]([CH3:24])=[C:12]([CH3:23])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54541847HCID 54541847, compound

Product 1

HCID 67690574HCID 67690574, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-(2-chlorophenyl)-6,7-dimethyl-3-quinolinecarboxylic acid ethyl ester (26.5 g), sodium borohydride (6.0 g) and ethanol (150 ml) was heated under reflux for 2 hours. After the solvent was distilled off, water was added to the residue, followed by extraction with ethyl acetate. After the extract was washed with water and dried, the solvent was distilled off. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=3:1) to yield 4-(2-chlorophenyl)-1,4-dihydro-6,7-dimethyl-3-quinolinecarboxylic acid ethyl ester as colorless crystals (5.0 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. distillationAfter the solvent was distilled off
  4. additionwater was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washAfter the extract was washed with water
  7. customdried
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-199d5374422c4b36abf3a669d17c3278
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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