Sodium Hydroxide → HCID 59807075, compound

HRID 1922368Notes

Reaction equation

HRID 1922368 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[N:1]1([CH2:6][CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59807051HCID 59807051, compound

Product 1

HCID 59807075HCID 59807075, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (700 mg, 2.87 mmol) in 12 mL anhydrous THF was treated with LiAlH4 (218 mg, 5.73 mmol) portionwise. The suspension was stirred at room temperature for 1 day. After this time, the mixture was cooled to 0° C. and treated with 2 mL 1N NaOH dropwise with rapid stirring. After stirring for 30 minutes, the suspension was treated with Na2SO4 and filtered. The filter cake was rinsed with CH2Cl2 (150 mL total). The filtrate was concentrated and the residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a light yellow oil (563 mg, 85.1%). 1H-NMR (CDCl3) δ: 7.06-7.01 (m, 1H), 6.93 (d, J=7.2 Hz, 1H), 6.63-6.52 (m, 2H), 3.44 (t, J=7.5 Hz, 2H), 3.31 (t, J=5.7 Hz, 2H), 2.76-2.56 (m, 8H), 1.97-1.90 (m, 2H), 1.83-1.78 (m, 4H).

Workup

  1. temperatureAfter this time, the mixture was cooled to 0° C.
  2. stirringAfter stirring for 30 minutes
  3. filtrationfiltered
  4. washThe filter cake was rinsed with CH2Cl2 (150 mL total)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2acc9da9ea344350a0fed57f8d2ee28d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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