Sodium borohydride → HCID 67690574, compound

HRID 375000Notes

Reaction equation

HRID 375000 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-9697be4a10614727a1e6e4c5f5ae5a55
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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