Methyl iodide → 2(1h)-Quinolinone,3-(2,6-dichloro-3-nitrophenyl)-1-methyl-

HRID 270700Notes

Reaction equation

HRID 270700 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13](=[O:22])[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.I[CH3:24]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13](=[O:22])[N:14]([CH3:24])[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 598339333-(2,6-dichloro-3-nitro-phenyl)-1H-quinolin-2-one

Product 1

HCID 598338082(1h)-Quinolinone,3-(2,6-dichloro-3-nitrophenyl)-1-methyl-Yield 35.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2,6-dichloro-3-nitro-phenyl)-1H-quinolin-2-one (0.21 g, 0.6266 mmol) in DMF (5.0 mL) is added HNa (30.1 mg, 60%, 0.752 mmol) and IMe (120.1 mg, 0.846 mmol) at 0° C. After the mixture is stirred for two hours at 0° C., the mixture is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by flash silica gel column, eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (95/5), t give the titled intermediate as a solid (78 mg, 35.8%).

Workup

  1. washwashed with saturated K2CO3, brine and water
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customis purified by flash silica gel column
  7. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (95/5), t

Sources & evidence

ORD record
ord-60dd77d7c65f4499bcef4f71040252c5
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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