Water → HCID 53392094, compound

HRID 1922348Notes

Reaction equation

HRID 1922348 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]1[CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 53392094HCID 53392094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (230 mg, 1.06 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (234 mg, 1.37 mmol) and potassium carbonate (440 mg, 3.18 mmol) in 5 mL DMF was stirred at room temperature for 4 days. After this time, the mixture was poured into 20 mL H2O then extracted with 2×30 mL CH2Cl2. The organic layers were combined together, washed with brine (20 mL) and concentrated. Product was subjected to flash chromatography on the biotage using 5% 2M NH3 in MeOH/CH2Cl2 to give a yellow solid. Yield: 218 mg of yellow solid (71%). 1H NMR (CDCl3) δ: 8.14 (dd, J=2.7, 9 Hz, 1H), 8.06 (d, J=2.4 Hz, 1H), 7.20 (d, J=9.0 Hz, 1H), 4.13 (t, J=7.5 Hz, 2H), 3.00 (t, J=6.9 Hz, 2H), 2.73-2.68 (m, 4H), 2.63-2.60 (m, 4H), 1.82-1.78 (m, 4H). MS (ESI): 290.2 (M+1, 100%).

Workup

  1. extractionthen extracted with 2×30 mL CH2Cl2
  2. washwashed with brine (20 mL)
  3. concentrationconcentrated
  4. customto give a yellow solid

Sources & evidence

ORD record
ord-07948fa9c7ea4fbbbae0c80672130731
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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