1-(2-morpholinoethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one → 6-amino-1-(2-morpholinoethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1922501Notes

Reaction equation

HRID 1922501 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=3)[CH2:12][CH2:11][C:10]2=[O:22])[CH2:3][CH2:2]1.[H][H]>[Pd].C(O)C>[NH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:9]([CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[C:10](=[O:22])[CH2:11][CH2:12]2

Participants

5

Reactant 2

HCID 598070771-(2-morpholinoethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 434465466-amino-1-(2-morpholinoethyl)-3,4-dihydroquinolin-2(1H)-oneYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of compound 2 (0.9211 g, 3.017 mmol) and palladium on carbon (10% wt, 0.092 g) in ethanol (10 mL) was stirred and fitted with a hydrogen balloon overnight. The suspension was filtered through a pad of celite and was rinsed with methanol (100 mL). The crude product was subject to flash chromatography on silica gel 2.5% 2M NH3 methanol/CH2Cl2, which resulted in a light brown solid, compound 3 (0.802 g, 96%).

Workup

  1. filtrationThe suspension was filtered through a pad of celite
  2. washwas rinsed with methanol (100 mL)

Sources & evidence

ORD record
ord-6ce8df24e32f4515a7faf4298e6f6198
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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