Sodium Hydroxide → HCID 59807132, compound

HRID 1922378Notes

Reaction equation

HRID 1922378 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH3:14])[C:7](=O)[CH2:6][CH2:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[N:15]1([CH:13]([CH3:14])[CH2:12][N:8]2[C:9]3[C:4](=[CH:3][C:2]([NH2:1])=[CH:11][CH:10]=3)[CH2:5][CH2:6][CH2:7]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59807033HCID 59807033, compound

Product 1

HCID 59807132HCID 59807132, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-amino-1-(2-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (245 mg, 0.90 mmol) in 10 mL anhydrous THF was cooled to 0° C. and treated with dropwise addition of 1M LiAlH4 in THF (2.7 mL, 2.7 mmol). The suspension was stirred at room temperature overnight. After this time, the mixture was cooled to 0° C. and treated with 1.5 mL 1N NaOH dropwise with rapid stirring. After stirring for 30 minutes, the suspension was diluted with 10 mL CH2Cl2 was treated with Na2SO4. The suspension was filtered and the solid was rinsed with 20 mL 5% 2M NH3 in MeOH/CH2Cl2. The filtrate was concentrated and the dark residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a dark viscous oil (136 mg, 58.4%). 1H-NMR (CDCl3) δ: 6.84 (br, 2H), 6.41 (br, 1H), 3.48 (dd, J=4.2, 14.4 Hz, 1H), 3.24-3.19 (m, 4H), 3.91 (dd, J=14.4, 4.2 Hz, 1H), 2.69-2.67 (m, 6H), 1.95-1.79 (m, 7H), 1.14 (d, J=6.6 Hz, 3H).

Workup

  1. temperatureAfter this time, the mixture was cooled to 0° C.
  2. stirringAfter stirring for 30 minutes
  3. filtrationThe suspension was filtered
  4. washthe solid was rinsed with 20 mL 5% 2M NH3 in MeOH/CH2Cl2
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-61a2bd522cae457daa2ea340098ef934
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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