Water → HCID 53392092, compound

HRID 1922338Notes

Reaction equation

HRID 1922338 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].Cl.Cl[CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:18]([N:19]([CH2:22][CH3:23])[CH2:20][CH2:21][N:10]1[C:11]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 53392092HCID 53392092, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (400 mg, 2.08 mmol), 2-chloro-N,N-diethylethanamine hydrochloride (394 mg, 2.29 mmol) and potassium carbonate (862 mg, 6.24 mmol) in 10 mL DMF was stirred at room temperature overnight. After this time, the mixture was poured into 20 mL H2O then extracted with 2×50 mL CH2Cl2. The organic layer was separated, washed with brine and concentrated to give a yellow brown solid which was subjected to flash chromatography on silica gel using 5% MeOH/CH2Cl2 to give a yellow viscous oil (585 mg, 96.5%). 1H-NMR (CDCl3) δ: 8.16 (dd, J=2.5, 9 Hz, 1H), 8.06 (d, J=2.5 Hz, 1H), 7.23 (d, J=9.0 Hz, 1H), 4.07 (t, J=7.0 Hz, 2H), 3.00 (t, J=7.0 Hz, 2H), 2.73-2.55 (m, 8H), 1.01 (t, J=7.0 Hz, 6H).

Workup

  1. extractionthen extracted with 2×50 mL CH2Cl2
  2. customThe organic layer was separated
  3. washwashed with brine
  4. concentrationconcentrated
  5. customto give a yellow brown solid which

Sources & evidence

ORD record
ord-fbc3905d489c480a87c5db643f9a54e2
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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