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

HRID 1991303Notes

Reaction equation

HRID 1991303 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].[C:15]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH3:15][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]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 218779431-methyl-6-nitro-3,4-dihydroquinolin-2(1H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 1, 990 mg, 5.15 mmol) in DMF (3.0 mL) is added K2CO3 (855 mg, 1.2 equiv.) followed by MeI (0.64 mL, 2.0 equiv.). The resulting solution is stirred overnight at room temperature. Water (20 mL) is then added and the reaction mixture is extracted with ethyl acetate (20 mL×2) and washed with saline (20 mL). The organic layers are collected and dried over MgSO4. Solvent is removed to yield the title compound as a yellow solid (956 mg, 90%). 1H NMR (300 MHz, DMSO) δ 8.16-7.26 (m, 3H), 3.30 (s, 3H), 3.00 (t, 2H), 2.61 (m, 2H).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate (20 mL×2)
  2. washwashed with saline (20 mL)
  3. customThe organic layers are collected
  4. dry with materialdried over MgSO4
  5. customSolvent is removed

Sources & evidence

ORD record
ord-b3dc525c4e374e41a575b78741c4ccb1
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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