Water → HCID 57861266, compound

HRID 1518059Notes

Reaction equation

HRID 1518059 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-673a44adfd8746c7be000832cbfd0a8c
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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