Methyl iodide → HCID 58424987, compound

HRID 2409418Notes

Reaction equation

HRID 2409418 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:8](=[O:15])[C:9]3[CH2:10][CH2:11][CH2:12][NH:13][C:14]=3[C:5]=2[CH:4]=1.[H-].[Na+].I[CH3:30]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:8](=[O:15])[C:9]3[CH2:10][CH2:11][CH2:12][N:13]([CH3:30])[C:14]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58424957HCID 58424957, compound

Product 1

HCID 58424987HCID 58424987, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-methoxy-6-(4-methoxybenzyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one (500 mg, 1.36 mmol) was dissolved in N,N-dimethylformamide (10 ml), added with sodium hydride (140 mg, 2.04 mmol) at 0° C. After stirring for 30 minutes, iodomethane (0.13 ml, 2.04 mmol) was added and the resulting mixture was stirred for 3 hours at 0° C. After completion, the mixture was poured into ice water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (hexane:ethyl acetate=1:1) to obtain the title compound (445 mg, yield: 90%, white solid).

Workup

  1. stirringthe resulting mixture was stirred for 3 hours at 0° C
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was then purified by flash column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a74757cd635e4273aecc3f9ac5b81701
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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