Water → HCID 57861266, compound

HRID 1960015Notes

Reaction equation

HRID 1960015 reaction equation
[CH:1]1([CH2:6][N:7]([C:10]2[C:19]([CH:20]=[O:21])=[CH:18][C:17]3[C:12](=[CH:13][C:14]([F:23])=[C:15]([F:22])[CH:16]=3)[N:11]=2)[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[Cl-].[NH4+].O>C(O)C>[CH:1]1([CH2:6][N:7]([C:10]2[C:19]([CH2:20][OH:21])=[CH:18][C:17]3[C:12](=[CH:13][C:14]([F:23])=[C:15]([F:22])[CH:16]=3)[N:11]=2)[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 57861271HCID 57861271, compound

Product 1

HCID 57861266HCID 57861266, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-[N-(cyclopentylmethyl)-N-ethylamino]-6,7-difluoroquinoline-3-carbaldehyde (0.10 g, 0.31 mmol) in ethanol (2.0 mL) is added sodium borohydride (14 mg, 0.37 mmol) and the mixture is stirred for 2 hours. After addition of sat. ammonium chloride and water, the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated to {2-[N-(cyclopentylmethyl)-N-ethylamino]-6,7-difluoroquinolin-3-yl}methanol which is used without further purification.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to {2-[N-(cyclopentylmethyl)-N-ethylamino]-6,7-difluoroquinolin-3-yl}methanol which
  6. customis used without further purification

Sources & evidence

ORD record
ord-9ee3afd60f3a43d58e8764f1895ea6e2
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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