Water → 1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one

HRID 1922359Notes

Reaction equation

HRID 1922359 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].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:10]2[C:11]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=3)[CH2:7][CH2:8][C:9]2=[O:14])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 598070541-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-oneYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 2.60 mmol), 4-methoxybenzyl chloride (388 μL, 2.86 mmol) and potassium carbonate (1.08 g, 7.80 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 solid which was subjected to flash chromatography on silica gel using 1% MeOH/CH2Cl2 to give an off-white solid (605 mg, 74.5%). 1H-NMR (DMSO-d6) δ: 8.15 (d, J=2.7 Hz, 1H), 8.02 (dd, J=2.7, 9.0 Hz, 1H), 7.15 (dd, J=3.0, 9.0 Hz, 1H), 6.88-6.85 (m, 4H), 5.14 (s, 2H), 3.70 (s, 3H), 3.11-3.06 (m, 2H), 2.80-2.75 (m, 2H).

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 solid which

Sources & evidence

ORD record
ord-af82832f1f2748fdb7f9ed2e9ba92ad5
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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