Methyl iodide → HCID 11127094, compound

HRID 1045362Notes

Reaction equation

HRID 1045362 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([CH:12]=[O:13])=[CH:11][C:4]=2[NH:3]1.CI.[C:16](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:16][N:3]1[C:2](=[O:1])[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([CH:12]=[O:13])=[CH:11][C:4]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 107736383-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

Product 1

HCID 11127094HCID 11127094, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde (0.5 g, 2.82 mmol), methyl iodide (0.6 g, 4.23 mmol) and cesium carbonate (1.37 g, 4.23 mmol) were dissolved in dry dimethylformamide (2 mL). The reaction mixture was irradiated by microwave at 100° C. for 30 minutes. The solvent was removed and the residue was washed with water and extracted with dichloromethane. Purification by silica chromatography (ISCO) produced 4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde (0.46 g, 85%). 1H NMR (400 MHz, DMSO-d6): δ 9.95 (s, 1H), 7.62 (s, 1H), 7.59 (d, 1H), 7.20 (d, 1H), 4.80 (s, 2H), 3.34 (s, 3H); MS (ESI) m/z: Calculated for C10H9NO3: 191.1. found: 192.1 (M+H)+.

Workup

  1. customThe reaction mixture was irradiated by microwave at 100° C. for 30 minutes
  2. customThe solvent was removed
  3. washthe residue was washed with water
  4. extractionextracted with dichloromethane
  5. customPurification by silica chromatography (ISCO)

Sources & evidence

ORD record
ord-8a954bfe94d6477fa2b47fbaa0434913
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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