Methyl iodide → HCID 45117446, compound

HRID 494203Notes

Reaction equation

HRID 494203 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16]I>CN(C=O)C>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[N:9]2[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 882777-Amino-4-methyl-2-quinolinone

Product 1

HCID 45117446HCID 45117446, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-amino-4-methyl-1H-quinolin-2-one (87 mg, 0.5 mmol) in dry DMF (2 ml) was added sodium hydride (24 mg, 60% disp. in oil, 0.6 mmol) followed by methyl iodide (38 μl, 0.6 mmol) and the reaction stirred at room temperature for 1.5 h. After quenching with water the mixture was extracted with EtOAc and the combined extracts were dried over MgSO4 and concentrated in vacuo to give the crude product. Purification by SPE column chromatography, eluting with 0-10% MeOH/EtOAc gradient gave title compound (64 mg) which was used in the next step without further purification. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.47 (d, 1H), 6.59 (m, 2H), 6.55 (d, 1H), 4.45 (br, 2H), 3.61 (s, 3H), 2.38 (s, 3H).

Workup

  1. customAfter quenching with water the mixture
  2. extractionwas extracted with EtOAc
  3. dry with materialthe combined extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customPurification by SPE column chromatography
  7. washeluting with 0-10% MeOH/EtOAc gradient

Sources & evidence

ORD record
ord-4d7165b32ecf4dc3ab561addde634058
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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