HCID 53392262, compound → HCID 28419113, compound

HRID 1922469Notes

Reaction equation

HRID 1922469 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:19]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([NH2:16])=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)[CH3:20]

Participants

5

Reactant 2

HCID 53392262HCID 53392262, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 28419113HCID 28419113, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of N,N-diethyl-2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine (0.85 g, 3.06 mmol) and palladium on charcoal, 10% wt (0.163 g, 0.153 mmol) in ethanol (30 mL) was stirred at room temperature under a balloon of hydrogen overnight. The mixture was filtered through a pad of celite. The celite pad was rinsed with 20 mL of methanol. The filtrate was concentrated and the residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in methanol/95% CH2Cl2 to give a dark brown residue (685 mg, 90%). 1H-NMR (CDCl3) δ 6.63-6.32 (m, 3H), 3.37-3.23 (m, 4H), 2.74-2.56 (m, 8H), 1.93 (t, J=5.7 Hz, 2H), 1.08 (t, J=7.2 Hz, 6H). MS (ESI): 248.2 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washThe celite pad was rinsed with 20 mL of methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-88648c1cf32f4361925b831fb5b91413
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…